JPS6059227B2 - Ｎ−ヒドロキシ低級アルキル−２−ニトロ低級アルキレンピロリジンおよびその製造法 - Google Patents
Ｎ−ヒドロキシ低級アルキル−２−ニトロ低級アルキレンピロリジンおよびその製造法Info
- Publication number
- JPS6059227B2 JPS6059227B2 JP51068167A JP6816776A JPS6059227B2 JP S6059227 B2 JPS6059227 B2 JP S6059227B2 JP 51068167 A JP51068167 A JP 51068167A JP 6816776 A JP6816776 A JP 6816776A JP S6059227 B2 JPS6059227 B2 JP S6059227B2
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- pyrrolidine
- nitro
- formula
- nitromethylenepyrrolidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 15
- -1 alkylene pyrrolidine Chemical compound 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- GPRSTIIZOTUISG-UHFFFAOYSA-N 2-[2-(nitromethylidene)pyrrolidin-1-yl]ethanol Chemical compound OCCN1CCCC1=C[N+]([O-])=O GPRSTIIZOTUISG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- LMDOTPWVWNPVEW-UHFFFAOYSA-N 3-[2-(nitromethylidene)pyrrolidin-1-yl]propan-1-ol Chemical compound OCCCN1CCCC1=C[N+]([O-])=O LMDOTPWVWNPVEW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003474 anti-emetic effect Effects 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000376 reactant 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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- YVTYKRYVHZTBPJ-UHFFFAOYSA-N 3-(2-oxopyrrolidin-1-yl)propyl acetate Chemical compound CC(=O)OCCCN1CCCC1=O YVTYKRYVHZTBPJ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- 230000002411 adverse Effects 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 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
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- FEZBIKUBAYAZIU-UHFFFAOYSA-N trimethobenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=CC(OCCN(C)C)=CC=2)=C1 FEZBIKUBAYAZIU-UHFFFAOYSA-N 0.000 description 1
- 229960004161 trimethobenzamide Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518175A FR2314177A1 (fr) | 1975-06-09 | 1975-06-09 | Nouvelles n-alkanol amines heterocycliques substituees, leurs derives, leurs procedes de preparation |
| FR7518175 | 1975-06-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51149269A JPS51149269A (en) | 1976-12-22 |
| JPS6059227B2 true JPS6059227B2 (ja) | 1985-12-24 |
Family
ID=9156325
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51068166A Granted JPS51149268A (en) | 1975-06-09 | 1976-06-09 | Nnalkanoll22substituted heterocyclic compounds and production thereof |
| JP51068167A Expired JPS6059227B2 (ja) | 1975-06-09 | 1976-06-09 | Ｎ−ヒドロキシ低級アルキル−２−ニトロ低級アルキレンピロリジンおよびその製造法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51068166A Granted JPS51149268A (en) | 1975-06-09 | 1976-06-09 | Nnalkanoll22substituted heterocyclic compounds and production thereof |
Country Status (35)
| Country | Link |
|---|---|
| JP (2) | JPS51149268A (no) |
| AR (1) | AR211927A1 (no) |
| AT (1) | AT349456B (no) |
| AU (1) | AU504920B2 (no) |
| BE (1) | BE842058A (no) |
| BG (1) | BG24800A3 (no) |
| CA (1) | CA1077949A (no) |
| CH (1) | CH614939A5 (no) |
| CS (1) | CS188284B2 (no) |
| DD (1) | DD125072A5 (no) |
| DE (1) | DE2623000A1 (no) |
| DK (1) | DK251876A (no) |
| EG (1) | EG13867A (no) |
| ES (1) | ES448642A1 (no) |
| FI (1) | FI761641A7 (no) |
| FR (1) | FR2314177A1 (no) |
| GB (2) | GB1499708A (no) |
| HK (1) | HK63679A (no) |
| HU (1) | HU171835B (no) |
| IE (1) | IE43228B1 (no) |
| IL (1) | IL49595A (no) |
| IN (1) | IN141747B (no) |
| LU (1) | LU75097A1 (no) |
| MC (1) | MC1104A1 (no) |
| MW (1) | MW1576A1 (no) |
| NL (1) | NL188526C (no) |
| NO (1) | NO761886L (no) |
| OA (1) | OA05344A (no) |
| PH (1) | PH15172A (no) |
| PT (1) | PT65163B (no) |
| RO (1) | RO69253A (no) |
| SE (1) | SE410852B (no) |
| YU (1) | YU39966B (no) |
| ZA (1) | ZA763041B (no) |
| ZM (1) | ZM6476A1 (no) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2684965A (en) * | 1950-08-10 | 1954-07-27 | Abbott Lab | Aminoalkylpiperidines |
-
1975
- 1975-06-09 FR FR7518175A patent/FR2314177A1/fr active Granted
-
1976
- 1976-05-17 IL IL49595A patent/IL49595A/xx unknown
- 1976-05-20 MC MC761197A patent/MC1104A1/xx unknown
- 1976-05-21 BE BE1007403A patent/BE842058A/xx not_active IP Right Cessation
- 1976-05-21 ZA ZA763041A patent/ZA763041B/xx unknown
- 1976-05-22 DE DE19762623000 patent/DE2623000A1/de not_active Withdrawn
- 1976-05-24 AR AR263373A patent/AR211927A1/es active
- 1976-05-25 AU AU14259/76A patent/AU504920B2/en not_active Expired
- 1976-05-27 IN IN925/CAL/76A patent/IN141747B/en unknown
- 1976-05-28 YU YU1310/76A patent/YU39966B/xx unknown
- 1976-06-01 IE IE1165/76A patent/IE43228B1/en unknown
- 1976-06-01 AT AT399876A patent/AT349456B/de not_active IP Right Cessation
- 1976-06-01 PT PT65163A patent/PT65163B/pt unknown
- 1976-06-02 RO RO7686326A patent/RO69253A/ro unknown
- 1976-06-03 NO NO761886A patent/NO761886L/no unknown
- 1976-06-03 ZM ZM64/76A patent/ZM6476A1/xx unknown
- 1976-06-04 LU LU75097A patent/LU75097A1/xx unknown
- 1976-06-04 BG BG033361A patent/BG24800A3/xx unknown
- 1976-06-04 CS CS763723A patent/CS188284B2/cs unknown
- 1976-06-05 OA OA55841A patent/OA05344A/xx unknown
- 1976-06-07 ES ES448642A patent/ES448642A1/es not_active Expired
- 1976-06-08 GB GB18917/77A patent/GB1499708A/en not_active Expired
- 1976-06-08 SE SE7606425A patent/SE410852B/xx not_active IP Right Cessation
- 1976-06-08 GB GB23694/76A patent/GB1499707A/en not_active Expired
- 1976-06-08 DK DK251876A patent/DK251876A/da unknown
- 1976-06-09 FI FI761641A patent/FI761641A7/fi not_active Application Discontinuation
- 1976-06-09 CH CH730176A patent/CH614939A5/xx not_active IP Right Cessation
- 1976-06-09 JP JP51068166A patent/JPS51149268A/ja active Granted
- 1976-06-09 MW MW15/76A patent/MW1576A1/xx unknown
- 1976-06-09 HU HU76SO00001170A patent/HU171835B/hu unknown
- 1976-06-09 NL NLAANVRAGE7606241,A patent/NL188526C/xx not_active IP Right Cessation
- 1976-06-09 JP JP51068167A patent/JPS6059227B2/ja not_active Expired
- 1976-06-09 CA CA254,481A patent/CA1077949A/en not_active Expired
- 1976-06-09 DD DD193271A patent/DD125072A5/xx not_active IP Right Cessation
- 1976-06-20 EG EG325/76A patent/EG13867A/xx active
-
1979
- 1979-09-06 HK HK636/79A patent/HK63679A/xx unknown
-
1980
- 1980-04-25 PH PH23958A patent/PH15172A/en unknown
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