DE2556326A1 - Neue pyrrolidone und verfahren zu ihrer herstellung - Google Patents
Neue pyrrolidone und verfahren zu ihrer herstellungInfo
- Publication number
- DE2556326A1 DE2556326A1 DE19752556326 DE2556326A DE2556326A1 DE 2556326 A1 DE2556326 A1 DE 2556326A1 DE 19752556326 DE19752556326 DE 19752556326 DE 2556326 A DE2556326 A DE 2556326A DE 2556326 A1 DE2556326 A1 DE 2556326A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- pyrrolidone
- meaning given
- carbon atoms
- 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.)
- Pending
Links
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- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000004040 pyrrolidinones Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 93
- -1 amine salts Chemical class 0.000 claims description 36
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 150000002902 organometallic compounds Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
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- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000002089 prostaglandin antagonist Substances 0.000 description 1
- 230000002997 prostaglandinlike Effects 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000003033 spasmogenic effect Effects 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752556326 DE2556326A1 (de) | 1975-12-13 | 1975-12-13 | Neue pyrrolidone und verfahren zu ihrer herstellung |
| CA255,666A CA1085859A (en) | 1975-06-27 | 1976-06-25 | Pyrrolidones and process for their manufacture |
| NL7613643A NL7613643A (nl) | 1975-12-13 | 1976-12-08 | Werkwijze voor het bereiden van pyrrolidonen. |
| DK554776A DK554776A (da) | 1975-12-13 | 1976-12-10 | Prostaglandinanaloge pyrrolidoner samt deres fremstilling og anvendelse |
| AU20473/76A AU2047376A (en) | 1975-12-13 | 1976-12-10 | Pyrrolidones |
| SE7613948A SE7613948L (sv) | 1975-12-13 | 1976-12-10 | Nya pyrrolidoner och forfarande for deras framstellning |
| ZA767379A ZA767379B (en) | 1975-12-13 | 1976-12-10 | Novel pyrrolidones and process for their manufacture |
| IL51090A IL51090A0 (en) | 1975-12-13 | 1976-12-10 | Novel pyrrolidones and process for their manufacture |
| LU76367A LU76367A1 (enrdf_load_stackoverflow) | 1975-12-13 | 1976-12-10 | |
| GB51912/76A GB1569982A (en) | 1975-12-13 | 1976-12-13 | Pyrrolidones and process for their manufacture |
| JP51148823A JPS5273865A (en) | 1975-12-13 | 1976-12-13 | Production of novel pyrrolidone |
| FR7637469A FR2334352A2 (fr) | 1975-12-13 | 1976-12-13 | Pyrrolidones et medicaments qui en contiennent |
| CA267,691A CA1072108A (en) | 1975-12-13 | 1976-12-13 | Pyrrolidones and process for their manufacture |
| BE173206A BE849346R (fr) | 1975-12-13 | 1976-12-13 | Pyrrolidones et medicaments qui en contiennent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752556326 DE2556326A1 (de) | 1975-12-13 | 1975-12-13 | Neue pyrrolidone und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2556326A1 true DE2556326A1 (de) | 1977-06-23 |
Family
ID=5964379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752556326 Pending DE2556326A1 (de) | 1975-06-27 | 1975-12-13 | Neue pyrrolidone und verfahren zu ihrer herstellung |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0325984A3 (en) * | 1988-01-25 | 1991-01-02 | Hoechst-Roussel Pharmaceuticals Incorporated | 5-substituted 1-/4-(1-pyrrolidinyl)-2-butynyl/-2-pyrrolidones and related compounds, a process for their preparation and their use as medicaments |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2254726T3 (es) | 2001-07-16 | 2006-06-16 | F. Hoffmann-La Roche Ag | Analogos de prostaglandina como agonistas receptores de ep4. |
| DK1408961T3 (da) | 2001-07-16 | 2007-11-05 | Hoffmann La Roche | 2 pyrrolidon-derivater som prostanoide agonister |
| MXPA04000757A (es) | 2001-07-23 | 2004-07-08 | Ono Pharmaceutical Co | Remedios para enfermedades con perdida de masa de hueso que tienen agonistas ep4 como ingrediente activo. |
| JP4547912B2 (ja) | 2002-03-05 | 2010-09-22 | 小野薬品工業株式会社 | ８−アザプロスタグランジン誘導体化合物およびその化合物を有効成分として含有する薬剤 |
| RU2311409C2 (ru) | 2003-01-10 | 2007-11-27 | Ф.Хоффманн-Ля Рош Аг | Производные 2-пиперидона в качестве агонистов простагландина |
| US7179820B2 (en) | 2003-06-06 | 2007-02-20 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
-
1975
- 1975-12-13 DE DE19752556326 patent/DE2556326A1/de active Pending
-
1976
- 1976-12-08 NL NL7613643A patent/NL7613643A/xx not_active Application Discontinuation
- 1976-12-10 DK DK554776A patent/DK554776A/da unknown
- 1976-12-10 SE SE7613948A patent/SE7613948L/xx unknown
- 1976-12-10 ZA ZA767379A patent/ZA767379B/xx unknown
- 1976-12-10 LU LU76367A patent/LU76367A1/xx unknown
- 1976-12-10 AU AU20473/76A patent/AU2047376A/en not_active Expired
- 1976-12-10 IL IL51090A patent/IL51090A0/xx unknown
- 1976-12-13 GB GB51912/76A patent/GB1569982A/en not_active Expired
- 1976-12-13 CA CA267,691A patent/CA1072108A/en not_active Expired
- 1976-12-13 FR FR7637469A patent/FR2334352A2/fr active Granted
- 1976-12-13 JP JP51148823A patent/JPS5273865A/ja active Pending
- 1976-12-13 BE BE173206A patent/BE849346R/xx active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0325984A3 (en) * | 1988-01-25 | 1991-01-02 | Hoechst-Roussel Pharmaceuticals Incorporated | 5-substituted 1-/4-(1-pyrrolidinyl)-2-butynyl/-2-pyrrolidones and related compounds, a process for their preparation and their use as medicaments |
Also Published As
| Publication number | Publication date |
|---|---|
| LU76367A1 (enrdf_load_stackoverflow) | 1977-06-28 |
| CA1072108A (en) | 1980-02-19 |
| FR2334352A2 (fr) | 1977-07-08 |
| SE7613948L (sv) | 1977-06-14 |
| BE849346R (fr) | 1977-06-13 |
| AU2047376A (en) | 1978-06-15 |
| DK554776A (da) | 1977-06-14 |
| GB1569982A (en) | 1980-06-25 |
| NL7613643A (nl) | 1977-06-15 |
| ZA767379B (en) | 1977-11-30 |
| IL51090A0 (en) | 1977-02-28 |
| JPS5273865A (en) | 1977-06-21 |
| FR2334352B2 (enrdf_load_stackoverflow) | 1978-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |