PT90614B - Processo para a preparacao de tienil-piperazinonas e de composicoes farmaceuticas que os contem - Google Patents
Processo para a preparacao de tienil-piperazinonas e de composicoes farmaceuticas que os contem Download PDFInfo
- Publication number
- PT90614B PT90614B PT90614A PT9061489A PT90614B PT 90614 B PT90614 B PT 90614B PT 90614 A PT90614 A PT 90614A PT 9061489 A PT9061489 A PT 9061489A PT 90614 B PT90614 B PT 90614B
- Authority
- PT
- Portugal
- Prior art keywords
- phenyl
- alkyl
- alkoxy
- compound
- thien
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000002253 acid Substances 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 239000013543 active substance Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 150000002902 organometallic compounds Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 3
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- BBACKDMGYMXYLE-UHFFFAOYSA-N 3-thiophen-2-ylpiperazin-2-one Chemical group O=C1NCCNC1C1=CC=CS1 BBACKDMGYMXYLE-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- SGMFROJGSXUXKY-UHFFFAOYSA-N 3-methyl-3-thiophen-2-ylpiperazin-2-one Chemical compound C=1C=CSC=1C1(C)NCCNC1=O SGMFROJGSXUXKY-UHFFFAOYSA-N 0.000 claims 1
- NSSFIMLPZOMBKC-UHFFFAOYSA-N 3-phenyl-3-thiophen-2-ylpiperazin-2-one Chemical compound O=C1NCCNC1(C=1C=CC=CC=1)C1=CC=CS1 NSSFIMLPZOMBKC-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- -1 3-Substituted 3-(thien-2-yl)piperazin-2-ones Chemical class 0.000 abstract description 197
- 230000001777 nootropic effect Effects 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 239000000126 substance Substances 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
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- 229910052749 magnesium Inorganic materials 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- 229920002472 Starch Polymers 0.000 description 4
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- 239000007903 gelatin capsule Substances 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
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- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- UXJHQIUBXZCLNA-UHFFFAOYSA-N 2-thiophen-2-yl-2,6-dihydro-1h-pyrazin-3-one Chemical compound O=C1N=CCNC1C1=CC=CS1 UXJHQIUBXZCLNA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical class O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3817198A DE3817198A1 (de) | 1988-05-20 | 1988-05-20 | Thienyl-piperazinone, ihre herstellung und verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT90614A PT90614A (pt) | 1989-11-30 |
| PT90614B true PT90614B (pt) | 1994-10-31 |
Family
ID=6354766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT90614A PT90614B (pt) | 1988-05-20 | 1989-05-19 | Processo para a preparacao de tienil-piperazinonas e de composicoes farmaceuticas que os contem |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4898866A (enExample) |
| EP (1) | EP0342536B1 (enExample) |
| JP (1) | JPH0217185A (enExample) |
| KR (1) | KR900018084A (enExample) |
| AT (1) | ATE80885T1 (enExample) |
| DE (2) | DE3817198A1 (enExample) |
| DK (1) | DK214589A (enExample) |
| ES (1) | ES2052807T3 (enExample) |
| GR (1) | GR3006577T3 (enExample) |
| HU (1) | HUT55388A (enExample) |
| PT (1) | PT90614B (enExample) |
| ZA (1) | ZA893766B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3909379A1 (de) * | 1989-03-22 | 1990-09-27 | Cassella Ag | Thienylpiperazine, verfahren zu ihrer herstellung, ihre verwendung sowie diese enthaltende arzneimittel und deren herstellung |
| DE69919707T2 (de) | 1998-06-19 | 2005-09-01 | Chiron Corp., Emeryville | Glycogen synthase kinase 3 inhibitoren |
| US7045519B2 (en) * | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| JP5352168B2 (ja) | 2008-09-12 | 2013-11-27 | 日本コヴィディエン株式会社 | 医療用針と医療用チューブの接続構造 |
| SG172008A1 (en) * | 2008-12-31 | 2011-07-28 | Kci Licensing Inc | Manifolds, systems, and methods for administering reduced pressure to a subcutaneous tissue site |
| EP2683431B1 (en) | 2011-03-09 | 2017-01-18 | Chong Corporation | Medicant delivery system |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2653153A (en) * | 1952-02-08 | 1953-09-22 | Rohm & Haas | 4-n-substituted-2-ketopiperazines |
| US3056784A (en) * | 1960-10-03 | 1962-10-02 | Richardson Merrell Inc | Substituted 5, 6-dihydro-2(1h)-pyrazinones |
| DE1197089B (de) * | 1962-01-25 | 1965-07-22 | Richardson Merrell Inc | Verfahren zur Herstellung von 2-Oxo-1, 2, 5, 6-tetrahydropyrazinen |
| US3390139A (en) * | 1964-03-04 | 1966-03-11 | Rohm & Haas | Nu-vinyl-2-piperazinones |
| DE3132882A1 (de) * | 1981-08-20 | 1983-03-03 | Cassella Ag, 6000 Frankfurt | Neue piperazinone, ihre herstellung und verwendung |
-
1988
- 1988-05-20 DE DE3817198A patent/DE3817198A1/de not_active Withdrawn
-
1989
- 1989-05-02 DK DK214589A patent/DK214589A/da not_active Application Discontinuation
- 1989-05-09 US US07/349,540 patent/US4898866A/en not_active Expired - Fee Related
- 1989-05-12 ES ES89108550T patent/ES2052807T3/es not_active Expired - Lifetime
- 1989-05-12 EP EP89108550A patent/EP0342536B1/de not_active Expired - Lifetime
- 1989-05-12 AT AT89108550T patent/ATE80885T1/de not_active IP Right Cessation
- 1989-05-12 DE DE8989108550T patent/DE58902320D1/de not_active Expired - Fee Related
- 1989-05-19 HU HU892509A patent/HUT55388A/hu unknown
- 1989-05-19 ZA ZA893766A patent/ZA893766B/xx unknown
- 1989-05-19 JP JP1124583A patent/JPH0217185A/ja active Pending
- 1989-05-19 PT PT90614A patent/PT90614B/pt not_active IP Right Cessation
- 1989-05-19 KR KR1019890006690A patent/KR900018084A/ko not_active Withdrawn
-
1992
- 1992-12-18 GR GR920402191T patent/GR3006577T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE80885T1 (de) | 1992-10-15 |
| ES2052807T3 (es) | 1994-07-16 |
| PT90614A (pt) | 1989-11-30 |
| JPH0217185A (ja) | 1990-01-22 |
| DE58902320D1 (de) | 1992-10-29 |
| DK214589D0 (da) | 1989-05-02 |
| ZA893766B (en) | 1990-02-28 |
| KR900018084A (ko) | 1990-12-20 |
| US4898866A (en) | 1990-02-06 |
| DE3817198A1 (de) | 1989-11-30 |
| EP0342536B1 (de) | 1992-09-23 |
| EP0342536A1 (de) | 1989-11-23 |
| GR3006577T3 (enExample) | 1993-06-30 |
| HUT55388A (en) | 1991-05-28 |
| DK214589A (da) | 1989-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG3A | Patent granted, date of granting |
Effective date: 19940408 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19951031 |