CA1115212A - Pyrrolidine derivatives - Google Patents
Pyrrolidine derivativesInfo
- Publication number
- CA1115212A CA1115212A CA319,572A CA319572A CA1115212A CA 1115212 A CA1115212 A CA 1115212A CA 319572 A CA319572 A CA 319572A CA 1115212 A CA1115212 A CA 1115212A
- Authority
- CA
- Canada
- Prior art keywords
- methoxybenzyl
- formula
- test
- medicament
- dosage
- 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
- 150000003235 pyrrolidines Chemical class 0.000 title description 2
- -1 o-methoxybenzoyl Chemical group 0.000 claims abstract description 15
- 230000002490 cerebral effect Effects 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims abstract description 4
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims abstract 3
- 239000003937 drug carrier Substances 0.000 claims 2
- JFXXBYZUNOVBOQ-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)CCC1 JFXXBYZUNOVBOQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- 239000007903 gelatin capsule Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229960004424 carbon dioxide Drugs 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229960003878 haloperidol Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000005069 ears Anatomy 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000282695 Saimiri Species 0.000 description 1
- 241000282696 Saimiri sciureus Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003953 γ-lactams Chemical class 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
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1404/78 | 1978-02-10 | ||
| CH140478 | 1978-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1115212A true CA1115212A (en) | 1981-12-29 |
Family
ID=4209637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA319,572A Expired CA1115212A (en) | 1978-02-10 | 1979-01-12 | Pyrrolidine derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4239770A (enExample) |
| EP (1) | EP0003602B1 (enExample) |
| JP (1) | JPS54117469A (enExample) |
| AU (1) | AU525204B2 (enExample) |
| CA (1) | CA1115212A (enExample) |
| DE (1) | DE2967324D1 (enExample) |
| IE (1) | IE48897B1 (enExample) |
| IL (1) | IL56577A (enExample) |
| MC (1) | MC1258A1 (enExample) |
| NZ (1) | NZ189572A (enExample) |
| PH (1) | PH14270A (enExample) |
| ZA (1) | ZA79452B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1131959B (it) * | 1979-08-09 | 1986-06-25 | Hoffmann La Roche | Derivati pirrolidinici |
| CH646149A5 (de) * | 1981-02-05 | 1984-11-15 | Hoffmann La Roche | Pyrrolidin-derivat. |
| US4431662A (en) * | 1981-03-06 | 1984-02-14 | Hodgson Gordon L Jun | 1-(1,3-Benzodioxol-5-yl)-2-pyrrolidinone and its medicinal use |
| EP0106988A1 (en) * | 1982-09-02 | 1984-05-02 | The Wellcome Foundation Limited | Pharmacologically active lactam derivatives |
| DE3336024A1 (de) * | 1983-10-04 | 1985-04-18 | Boehringer Ingelheim KG, 6507 Ingelheim | 4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel |
| DE3706399A1 (de) * | 1987-02-27 | 1988-09-08 | Boehringer Ingelheim Kg | Mittel mit antidepressiver wirkung |
| IT1215587B (it) * | 1987-06-26 | 1990-02-14 | Roussel Maestretti Spa | Derivati della 1-benzoil2-oxo 5-alcossi pirrolidina, loro procedimento di preparazione e loro impiego come sostanza medicinale. |
| IT1231921B (it) * | 1989-06-12 | 1992-01-15 | Sigma Tau Ind Farmaceuti | 1-acil-2-pirrolidoni quali attivatori dei processi di apprendimento e della memoria e composizioni farmaceutiche comprendenti tali composti |
| JP2803882B2 (ja) * | 1990-02-20 | 1998-09-24 | 日清製粉株式会社 | １―フエノキシカルボニル―２―ピロリジノン誘導体 |
| IT1242043B (it) * | 1990-12-21 | 1994-02-02 | Sigma Tau Ind Farmaceuti | Derivati della 1,2,3,4,-tetraidronaftilammina ad attivita' nootropica e composizioni farmaceutiche che li contengono. |
| US5780375A (en) * | 1993-10-19 | 1998-07-14 | E. I. Du Pont De Nemours And Company | Thick film composition for modifying the electrical properties of a dielectric layer |
| EP3068782B1 (en) * | 2013-11-13 | 2018-05-23 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2915430A (en) * | 1958-09-30 | 1959-12-01 | Gen Aniline & Film Corp | Method of controlling nematodes with n-acylpyrrolidones |
| GB1039113A (en) | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
| ES425600A1 (es) * | 1974-04-23 | 1977-01-16 | Lafarquim | Procedimiento de obtencion de un nuevo derivado de pirroli- dinona. |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
| ES433723A1 (es) * | 1975-01-10 | 1976-11-16 | Lafarquim S A Lab | Procedimiento de obtencion de un derivado de 2-pirrolidi- nona. |
| DE2616374A1 (de) * | 1976-04-14 | 1977-10-27 | Bayer Ag | In 4-stellung amidoalkylierte phenole |
-
1979
- 1979-01-12 CA CA319,572A patent/CA1115212A/en not_active Expired
- 1979-01-25 PH PH22106A patent/PH14270A/en unknown
- 1979-02-02 US US06/008,674 patent/US4239770A/en not_active Expired - Lifetime
- 1979-02-02 ZA ZA79452A patent/ZA79452B/xx unknown
- 1979-02-02 AU AU43889/79A patent/AU525204B2/en not_active Ceased
- 1979-02-02 IL IL56577A patent/IL56577A/xx unknown
- 1979-02-05 NZ NZ189572A patent/NZ189572A/en unknown
- 1979-02-08 JP JP1288179A patent/JPS54117469A/ja active Granted
- 1979-02-08 MC MC791363A patent/MC1258A1/fr unknown
- 1979-02-09 DE DE7979100378T patent/DE2967324D1/de not_active Expired
- 1979-02-09 EP EP79100378A patent/EP0003602B1/de not_active Expired
- 1979-02-09 IE IE245/79A patent/IE48897B1/en unknown
-
1980
- 1980-02-19 US US06/122,646 patent/US4349562A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL56577A (en) | 1982-07-30 |
| AU525204B2 (en) | 1982-10-28 |
| PH14270A (en) | 1981-04-29 |
| IL56577A0 (en) | 1979-05-31 |
| NZ189572A (en) | 1985-01-31 |
| JPS54117469A (en) | 1979-09-12 |
| IE790245L (en) | 1979-08-10 |
| US4349562A (en) | 1982-09-14 |
| EP0003602B1 (de) | 1984-12-12 |
| MC1258A1 (fr) | 1980-01-14 |
| DE2967324D1 (en) | 1985-01-24 |
| AU4388979A (en) | 1979-08-16 |
| EP0003602A1 (de) | 1979-08-22 |
| IE48897B1 (en) | 1985-06-12 |
| JPS6210206B2 (enExample) | 1987-03-05 |
| US4239770A (en) | 1980-12-16 |
| ZA79452B (en) | 1980-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |