GB1350582A - Cerivatives of 2-pyrrolidinone - Google Patents
Cerivatives of 2-pyrrolidinoneInfo
- Publication number
- GB1350582A GB1350582A GB3594870A GB1350582DA GB1350582A GB 1350582 A GB1350582 A GB 1350582A GB 3594870 A GB3594870 A GB 3594870A GB 1350582D A GB1350582D A GB 1350582DA GB 1350582 A GB1350582 A GB 1350582A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- alkyl
- hydrogen atom
- para
- radical
- 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000005907 alkyl ester group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- JMVIVASFFKKFQK-UHFFFAOYSA-N 1-phenylpyrrolidin-2-one Chemical class O=C1CCCN1C1=CC=CC=C1 JMVIVASFFKKFQK-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 239000012954 diazonium Substances 0.000 abstract 2
- 150000001989 diazonium salts Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NJBMZYSKLWQXLJ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-amine Chemical compound NC1=NCCC1 NJBMZYSKLWQXLJ-UHFFFAOYSA-N 0.000 abstract 1
- BXYQHDXDCJQOFD-UHFFFAOYSA-N 3-cyanopropanoic acid Chemical compound OC(=O)CCC#N BXYQHDXDCJQOFD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 229940114081 cinnamate Drugs 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- VSXUOQHNVXKVMC-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-4-nitropentanoate Chemical compound CCOC(=O)CC(C(C)[N+]([O-])=O)C1=CC=C(Cl)C=C1 VSXUOQHNVXKVMC-UHFFFAOYSA-N 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
-
- 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
-
- 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
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3594870 | 1970-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1350582A true GB1350582A (en) | 1974-04-18 |
Family
ID=10383283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3594870A Expired GB1350582A (en) | 1970-07-24 | 1970-07-24 | Cerivatives of 2-pyrrolidinone |
Country Status (26)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2923553A1 (de) | 1978-06-12 | 1979-12-20 | Mundipharma Ag | Verfahren zur herstellung von delta hoch 3 -pyrrolin-(2)-derivaten sowie verwendung von delta hoch 3 -pyrrolin-(2)- derivaten zur herstellung von pyrrolidon- (2)-derivaten |
| US4956473A (en) * | 1988-09-01 | 1990-09-11 | Lonza Ltd. | 2-aza-4-(alkoxycarbonyl)spiro[4,5]decan-3-one |
| US5131947A (en) * | 1989-03-15 | 1992-07-21 | Mitsui Toatsu Chemicals Incorporated | 4-ethyl-3-(substituted phenyl)-1-(3-trifluoromethylphenyl)-2-pyrrolidinone derivatives, herbicidal compositions containing them and use thereof |
| WO1992019594A1 (en) * | 1991-05-02 | 1992-11-12 | Smithkline Beecham Corporation | Pyrrolidinones |
| US5747516A (en) * | 1993-11-19 | 1998-05-05 | E. I. Du Pont De Nemours And Company | Dihydroazole compounds and their use for controlling fungal plant diseases |
| US6022870A (en) * | 1998-01-14 | 2000-02-08 | E. I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| WO2003067986A1 (de) * | 2002-02-13 | 2003-08-21 | Bayer Cropscience Ag | Delta1-pyrroline und deren verwendung zur bekämpfung von schädlingen |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2413935A1 (de) * | 1974-03-20 | 1975-10-16 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone |
| NL7412694A (nl) * | 1974-09-26 | 1976-03-30 | Stamicarbon | Werkwijze voor de bereiding van een pyrrolidon- -2. |
| DE2541855A1 (de) * | 1975-09-18 | 1977-03-31 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone ii |
| AU518986B2 (en) * | 1977-10-11 | 1981-10-29 | Takeda Chemical Industries Ltd. | Lactams |
| US4548947A (en) * | 1984-05-07 | 1985-10-22 | Warner-Lambert Company | 1-(Substituted-aryl)-dihydro-1H-pyrrolizine-3,5-[2H,6H-]diones and use for reversing amnesia |
| DE3823299A1 (de) * | 1988-07-07 | 1990-01-11 | Schering Ag | Substituierte phenyl-pyrrolidin-2-one, -oxazolidin-2-one und -imidazolidin-2-one, ihre herstellung sowie verwendung in arzneimitteln |
| WO1993007141A1 (en) * | 1991-10-11 | 1993-04-15 | Smithkline Beecham Corporation | Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR67024E (fr) * | 1954-10-22 | 1957-11-04 | Anciens Ets Barbier | Appareil d'éclairage |
| US2984672A (en) * | 1958-05-14 | 1961-05-16 | Rohm & Haas | Method for the preparation of pyrrolinones |
-
1970
- 1970-07-24 GB GB3594870A patent/GB1350582A/en not_active Expired
-
1971
- 1971-06-24 IL IL37147A patent/IL37147A/xx unknown
- 1971-07-19 NL NL7109930A patent/NL7109930A/xx unknown
- 1971-07-20 FR FR7126784A patent/FR2100946B1/fr not_active Expired
- 1971-07-21 FI FI2068/71A patent/FI55184C/fi active
- 1971-07-21 CS CS5382A patent/CS174822B2/cs unknown
- 1971-07-21 YU YU1921/71A patent/YU34671B/xx unknown
- 1971-07-21 RO RO7181864A patent/RO71354A/ro unknown
- 1971-07-21 DK DK358071AA patent/DK135584B/da unknown
- 1971-07-21 RO RO67732A patent/RO61127A/ro unknown
- 1971-07-21 ES ES393496A patent/ES393496A1/es not_active Expired
- 1971-07-21 CS CS6089A patent/CS174849B2/cs unknown
- 1971-07-21 HU HUUI178A patent/HU162344B/hu unknown
- 1971-07-22 BG BG019868A patent/BG20582A3/xx unknown
- 1971-07-22 IN IN132195A patent/IN132195B/en unknown
- 1971-07-22 BE BE770308A patent/BE770308A/xx not_active IP Right Cessation
- 1971-07-22 CA CA118,906A patent/CA954870A/en not_active Expired
- 1971-07-22 BG BG018136A patent/BG21025A3/xx unknown
- 1971-07-22 IT IT51830/71A patent/IT1046928B/it active
- 1971-07-22 DE DE2136571A patent/DE2136571C2/de not_active Expired
- 1971-07-22 JP JP5490271A patent/JPS5417734B1/ja active Pending
- 1971-07-23 AT AT180572A patent/AT310150B/de not_active IP Right Cessation
- 1971-07-23 PL PL1971149583A patent/PL82184B1/pl unknown
- 1971-07-23 ZA ZA714911A patent/ZA714911B/xx unknown
- 1971-07-23 SU SU1689301A patent/SU488410A3/ru active
- 1971-07-23 CH CH1016072A patent/CH537921A/fr not_active IP Right Cessation
- 1971-07-23 CH CH1085771A patent/CH538474A/fr not_active IP Right Cessation
- 1971-07-23 SU SU1891416A patent/SU479293A3/ru active
- 1971-07-23 AU AU31575/71A patent/AU461836B2/en not_active Expired
- 1971-07-23 SE SE7109515A patent/SE379347B/xx unknown
- 1971-07-23 AT AT643071A patent/AT304530B/de not_active IP Right Cessation
-
1975
- 1975-12-31 MY MY1975123A patent/MY7500123A/xx unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2923553A1 (de) | 1978-06-12 | 1979-12-20 | Mundipharma Ag | Verfahren zur herstellung von delta hoch 3 -pyrrolin-(2)-derivaten sowie verwendung von delta hoch 3 -pyrrolin-(2)- derivaten zur herstellung von pyrrolidon- (2)-derivaten |
| DE2954236C2 (enrdf_load_stackoverflow) * | 1978-06-12 | 1988-10-06 | Mundipharma Ag, Basel, Ch | |
| US4956473A (en) * | 1988-09-01 | 1990-09-11 | Lonza Ltd. | 2-aza-4-(alkoxycarbonyl)spiro[4,5]decan-3-one |
| US4958044A (en) * | 1988-09-01 | 1990-09-18 | Lonza Ltd. | 2-aza-4-(alkoxycarbonyl)spiro[4,5]-decan-3-one |
| US5131947A (en) * | 1989-03-15 | 1992-07-21 | Mitsui Toatsu Chemicals Incorporated | 4-ethyl-3-(substituted phenyl)-1-(3-trifluoromethylphenyl)-2-pyrrolidinone derivatives, herbicidal compositions containing them and use thereof |
| WO1992019594A1 (en) * | 1991-05-02 | 1992-11-12 | Smithkline Beecham Corporation | Pyrrolidinones |
| US5747516A (en) * | 1993-11-19 | 1998-05-05 | E. I. Du Pont De Nemours And Company | Dihydroazole compounds and their use for controlling fungal plant diseases |
| US5977149A (en) * | 1993-11-19 | 1999-11-02 | E. I. Du Pont De Nemours And Company | Dihydrotriazole compounds and their use for controlling fungal plant diseases |
| US6022870A (en) * | 1998-01-14 | 2000-02-08 | E. I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| WO2003067986A1 (de) * | 2002-02-13 | 2003-08-21 | Bayer Cropscience Ag | Delta1-pyrroline und deren verwendung zur bekämpfung von schädlingen |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |