SU607551A3 - Способ получени 2-аминометил- ( -оксиалкил/пирролидинов) - Google Patents
Способ получени 2-аминометил- ( -оксиалкил/пирролидинов)Info
- Publication number
- SU607551A3 SU607551A3 SU762362660A SU2362660A SU607551A3 SU 607551 A3 SU607551 A3 SU 607551A3 SU 762362660 A SU762362660 A SU 762362660A SU 2362660 A SU2362660 A SU 2362660A SU 607551 A3 SU607551 A3 SU 607551A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aminomethyl
- pyrrolidines
- oxyalkyl
- obtaining
- omega
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 2
- 150000003235 pyrrolidines Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- -1 for example Chemical compound 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JQXLWCCKZDDEMZ-UHFFFAOYSA-N 2-[2-(aminomethyl)pyrrolidin-1-yl]ethanol Chemical compound NCC1CCCN1CCO JQXLWCCKZDDEMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- YVTYKRYVHZTBPJ-UHFFFAOYSA-N 3-(2-oxopyrrolidin-1-yl)propyl acetate Chemical compound CC(=O)OCCCN1CCCC1=O YVTYKRYVHZTBPJ-UHFFFAOYSA-N 0.000 description 2
- LMDOTPWVWNPVEW-UHFFFAOYSA-N 3-[2-(nitromethylidene)pyrrolidin-1-yl]propan-1-ol Chemical compound OCCCN1CCCC1=C[N+]([O-])=O LMDOTPWVWNPVEW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CVDGNRZPDAXOQO-UHFFFAOYSA-N 1-(3-hydroxypropyl)pyrrolidin-2-one Chemical compound OCCCN1CCCC1=O CVDGNRZPDAXOQO-UHFFFAOYSA-N 0.000 description 1
- FWZALIHLFUDLNV-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1CCCC1=O FWZALIHLFUDLNV-UHFFFAOYSA-N 0.000 description 1
- GPRSTIIZOTUISG-UHFFFAOYSA-N 2-[2-(nitromethylidene)pyrrolidin-1-yl]ethanol Chemical compound OCCN1CCCC1=C[N+]([O-])=O GPRSTIIZOTUISG-UHFFFAOYSA-N 0.000 description 1
- RAYGQIXIIBTRCF-UHFFFAOYSA-N 3-[2-(aminomethyl)pyrrolidin-1-yl]propan-1-ol Chemical compound NCC1CCCN1CCCO RAYGQIXIIBTRCF-UHFFFAOYSA-N 0.000 description 1
- HWBLTYHIEYOAOL-UHFFFAOYSA-N Diisopropyl sulfate Chemical compound CC(C)OS(=O)(=O)OC(C)C HWBLTYHIEYOAOL-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518001A FR2313935A1 (fr) | 1975-06-10 | 1975-06-10 | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU607551A3 true SU607551A3 (ru) | 1978-05-15 |
Family
ID=9156239
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762362660A SU607551A3 (ru) | 1975-06-10 | 1976-06-07 | Способ получени 2-аминометил- ( -оксиалкил/пирролидинов) |
| SU762366253A SU645557A3 (ru) | 1975-06-10 | 1976-06-09 | Способ получени производных бензамида или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762366253A SU645557A3 (ru) | 1975-06-10 | 1976-06-09 | Способ получени производных бензамида или их солей |
Country Status (37)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| FR2415099A1 (fr) * | 1978-01-20 | 1979-08-17 | Ile De France | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
| FR2438650A1 (fr) * | 1978-10-11 | 1980-05-09 | Ile De France | N-(1-methyl 2-pyrrolidinyl methyl) 2,3-dimethoxy 5-methylsulfamoyl benzamide et ses derives, leurs methodes de preparation et leur application dans le traitement des troubles du bas appareil urinaire |
| JPS597160A (ja) * | 1982-06-28 | 1984-01-14 | ラボラトリーオス・デラグランヘ・エセ・ア | Ｎ−（１−プロピル−２−ピロリジニルメチル）−２−メトキシ−５−スルフアモイルベンズアミド、その製造方法およびこれを有効成分とする抗うつ剤 |
| US4820715A (en) * | 1984-06-28 | 1989-04-11 | Bristol-Myers Company | Anti-emetic quinuclidinyl benzamides |
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
| US5011992A (en) * | 1984-06-28 | 1991-04-30 | Bristol-Myers Squibb Company | Pharmacologically active substituted benzamides |
| JP3026845B2 (ja) * | 1991-02-20 | 2000-03-27 | 日清製粉株式会社 | ピペリジン誘導体 |
| RU2205009C1 (ru) * | 2002-03-27 | 2003-05-27 | Государственный научный центр - Институт биофизики | Противорвотное средство бензамид |
| US9375486B2 (en) | 2012-09-17 | 2016-06-28 | Nektar Therapeutics | Oligomer-containing benzamide-based compounds |
-
1975
- 1975-06-10 FR FR7518001A patent/FR2313935A1/fr active Granted
-
1976
- 1976-05-21 ZA ZA763042A patent/ZA763042B/xx unknown
- 1976-05-21 BE BE1007404A patent/BE842059A/xx not_active IP Right Cessation
- 1976-05-22 RO RO7686179A patent/RO70265A/ro unknown
- 1976-05-22 DE DE19762623075 patent/DE2623075A1/de not_active Withdrawn
- 1976-05-24 AR AR263374A patent/AR210888A1/es active
- 1976-05-27 IN IN926/CAL/1976A patent/IN142899B/en unknown
- 1976-05-27 AU AU14360/76A patent/AU506001B2/en not_active Expired
- 1976-05-28 YU YU1318/76A patent/YU39352B/xx unknown
- 1976-06-01 AT AT400176A patent/AT358571B/de not_active IP Right Cessation
- 1976-06-01 IE IE1166/76A patent/IE43375B1/en unknown
- 1976-06-01 PT PT65164A patent/PT65164B/pt unknown
- 1976-06-02 EG EG326/76A patent/EG12285A/xx active
- 1976-06-03 ZM ZM65/76A patent/ZM6576A1/xx unknown
- 1976-06-04 NZ NZ181072A patent/NZ181072A/xx unknown
- 1976-06-04 CS CS763724A patent/CS189007B2/cs unknown
- 1976-06-04 BG BG033362A patent/BG27360A3/xx unknown
- 1976-06-07 SU SU762362660A patent/SU607551A3/ru active
- 1976-06-07 PH PH18542A patent/PH13912A/en unknown
- 1976-06-08 LU LU75104A patent/LU75104A1/xx unknown
- 1976-06-08 GB GB23695/76A patent/GB1500105A/en not_active Expired
- 1976-06-08 ES ES448643A patent/ES448643A1/es not_active Expired
- 1976-06-08 DD DD193235A patent/DD124380A5/xx not_active IP Right Cessation
- 1976-06-08 JP JP51067553A patent/JPS6055503B2/ja not_active Expired
- 1976-06-08 SE SE7606424A patent/SE415971B/xx not_active IP Right Cessation
- 1976-06-09 MX MX76291U patent/MX3580E/es unknown
- 1976-06-09 DK DK255276A patent/DK255276A/da unknown
- 1976-06-09 PL PL1976190247A patent/PL103075B1/pl not_active IP Right Cessation
- 1976-06-09 HU HU76SO00001171A patent/HU172195B/hu unknown
- 1976-06-09 SU SU762366253A patent/SU645557A3/ru active
- 1976-06-09 NO NO761977A patent/NO146058C/no unknown
- 1976-06-09 CA CA254,480A patent/CA1064930A/en not_active Expired
- 1976-06-09 OA OA55847A patent/OA05350A/xx unknown
- 1976-06-10 PL PL1976190304A patent/PL102929B1/pl unknown
- 1976-06-10 MW MW16/76A patent/MW1676A1/xx unknown
- 1976-06-10 FI FI761669A patent/FI761669A7/fi not_active Application Discontinuation
- 1976-06-10 NL NLAANVRAGE7606284,A patent/NL186382C/xx not_active IP Right Cessation
- 1976-06-10 CH CH736076A patent/CH596175A5/xx not_active IP Right Cessation
-
1979
- 1979-07-12 HK HK469/79A patent/HK46979A/xx unknown
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