LT3518B - Method for preparing 3-(n-phenyl-acetilamino-piperidine)-2,6-dion - Google Patents
Method for preparing 3-(n-phenyl-acetilamino-piperidine)-2,6-dion Download PDFInfo
- Publication number
- LT3518B LT3518B LTIP681A LTIP681A LT3518B LT 3518 B LT3518 B LT 3518B LT IP681 A LTIP681 A LT IP681A LT IP681 A LTIP681 A LT IP681A LT 3518 B LT3518 B LT 3518B
- Authority
- LT
- Lithuania
- Prior art keywords
- reaction mixture
- dion
- target product
- phenylacetyl
- glutamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- -1 phenylacetyl halide Chemical class 0.000 claims abstract description 7
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims abstract description 6
- 229930182816 L-glutamine Natural products 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- ITESSSIUDOPQKI-UHFFFAOYSA-N 2-phenyl-n-piperidin-1-ylacetamide Chemical compound C1CCCCN1NC(=O)CC1=CC=CC=C1 ITESSSIUDOPQKI-UHFFFAOYSA-N 0.000 claims description 5
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/295,372 US4918193A (en) | 1989-01-11 | 1989-01-11 | Methods for preparing 3-[N-phenyl-acetylaminopiperidine]-2,6-dion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP681A LTIP681A (en) | 1995-01-31 |
| LT3518B true LT3518B (en) | 1995-11-27 |
Family
ID=23137420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP681A LT3518B (en) | 1989-01-11 | 1993-06-23 | Method for preparing 3-(n-phenyl-acetilamino-piperidine)-2,6-dion |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4918193A (ru) |
| KR (1) | KR0139204B1 (ru) |
| FI (1) | FI92391C (ru) |
| LT (1) | LT3518B (ru) |
| PH (1) | PH26099A (ru) |
| PL (1) | PL163552B1 (ru) |
| RU (1) | RU1809830C (ru) |
| UA (1) | UA15756A (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5463063A (en) * | 1993-07-02 | 1995-10-31 | Celgene Corporation | Ring closure of N-phthaloylglutamines |
| US7087219B2 (en) * | 2003-05-28 | 2006-08-08 | Stanislaw R. Burzynski | Toothpaste containing anticancer agents |
| US20060246016A1 (en) * | 2003-05-28 | 2006-11-02 | Burzynski Stanislaw R | Toothpaste containing anticancer agents |
| CN103232361A (zh) * | 2013-04-19 | 2013-08-07 | 苏州园方化工有限公司 | 一种n-苯乙酰基-l-谷氨酰胺 |
| CN104693108B (zh) * | 2013-12-06 | 2017-05-31 | 重庆博腾制药科技股份有限公司 | 一种布鲁顿酪氨酸激酶(Btk)中间体的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558057A (en) | 1981-12-15 | 1985-12-10 | Burzynski Stanislaw R | Purified antineoplaston fractions and methods of treating neoplastic disease |
-
1989
- 1989-01-11 US US07/295,372 patent/US4918193A/en not_active Expired - Lifetime
- 1989-11-13 PH PH39525A patent/PH26099A/en unknown
-
1990
- 1990-01-10 FI FI900129A patent/FI92391C/fi active IP Right Grant
- 1990-01-10 UA UA4742866A patent/UA15756A/uk unknown
- 1990-01-10 KR KR1019900000205A patent/KR0139204B1/ko not_active IP Right Cessation
- 1990-01-10 PL PL90283254A patent/PL163552B1/pl not_active IP Right Cessation
- 1990-01-10 RU SU904742866A patent/RU1809830C/ru active
-
1993
- 1993-06-23 LT LTIP681A patent/LT3518B/lt not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558057A (en) | 1981-12-15 | 1985-12-10 | Burzynski Stanislaw R | Purified antineoplaston fractions and methods of treating neoplastic disease |
Also Published As
| Publication number | Publication date |
|---|---|
| FI900129A0 (fi) | 1990-01-10 |
| FI92391C (fi) | 1994-11-10 |
| PH26099A (en) | 1992-02-06 |
| PL163552B1 (pl) | 1994-04-29 |
| FI92391B (fi) | 1994-07-29 |
| KR900011748A (ko) | 1990-08-02 |
| FI900129A (fi) | 1990-07-12 |
| US4918193A (en) | 1990-04-17 |
| KR0139204B1 (ko) | 1998-05-15 |
| LTIP681A (en) | 1995-01-31 |
| UA15756A (uk) | 1997-06-30 |
| RU1809830C (ru) | 1993-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 20090623 |