GB1574043A - Dextrorotatory propanones - Google Patents
Dextrorotatory propanones Download PDFInfo
- Publication number
- GB1574043A GB1574043A GB26168/79A GB2616879A GB1574043A GB 1574043 A GB1574043 A GB 1574043A GB 26168/79 A GB26168/79 A GB 26168/79A GB 2616879 A GB2616879 A GB 2616879A GB 1574043 A GB1574043 A GB 1574043A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propan
- trans
- methoxypiperid
- dextrorotatory
- acid
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title description 8
- 239000002253 acid Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 10
- -1 methoxypiperid-2-yl Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- VNZVBGRNVIBWEU-DTWKUNHWSA-N 1-[(2s,3r)-3-methoxypiperidin-2-yl]propan-2-one Chemical compound CO[C@@H]1CCCN[C@H]1CC(C)=O VNZVBGRNVIBWEU-DTWKUNHWSA-N 0.000 claims description 5
- DVSQBUUDEVNABC-OULXEKPRSA-N 1-[(2s,3r)-3-methoxypiperidin-2-yl]propan-2-one;hydrobromide Chemical compound Br.CO[C@@H]1CCCN[C@H]1CC(C)=O DVSQBUUDEVNABC-OULXEKPRSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000011369 resultant mixture Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DVSQBUUDEVNABC-UHFFFAOYSA-N 1-(3-methoxypiperidin-2-yl)propan-2-one;hydrobromide Chemical compound Br.COC1CCCNC1CC(C)=O DVSQBUUDEVNABC-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000002192 coccidiostatic effect Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- RFCXXKWROOFQSI-UHFFFAOYSA-N 7-bromo-6-chloro-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=C1C=C(Br)C(Cl)=C2 RFCXXKWROOFQSI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VNZVBGRNVIBWEU-UHFFFAOYSA-N 1-(3-methoxypiperidin-2-yl)propan-2-one Chemical compound COC1CCCNC1CC(C)=O VNZVBGRNVIBWEU-UHFFFAOYSA-N 0.000 description 1
- NOIFAAGDZNZRMA-DTWKUNHWSA-N 1-bromo-3-[(2s,3r)-3-methoxypiperidin-2-yl]propan-2-one Chemical compound CO[C@@H]1CCCN[C@H]1CC(=O)CBr NOIFAAGDZNZRMA-DTWKUNHWSA-N 0.000 description 1
- MRWRHHSVHWCISU-UHFFFAOYSA-N 3-methoxypiperidine Chemical compound COC1CCCNC1 MRWRHHSVHWCISU-UHFFFAOYSA-N 0.000 description 1
- FOKDVSBEPHQLEC-UHFFFAOYSA-N Br.O=c1nc[nH]c2ccccc12 Chemical compound Br.O=c1nc[nH]c2ccccc12 FOKDVSBEPHQLEC-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- YVGLSUJNDXBZBM-UHFFFAOYSA-N propan-2-one;hydrobromide Chemical compound Br.CC(C)=O YVGLSUJNDXBZBM-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7602413A FR2339402A1 (fr) | 1976-01-29 | 1976-01-29 | Nouvelle quinazolinone et ses sels, leurs procede de preparation et leur application comme medicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1574043A true GB1574043A (en) | 1980-09-03 |
Family
ID=9168514
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26168/79A Expired GB1574043A (en) | 1976-01-29 | 1977-01-28 | Dextrorotatory propanones |
| GB3615/77A Expired GB1574042A (en) | 1976-01-29 | 1977-01-28 | 3-(3-(3-hydroxypiperid-2-yl) acetonyl)-3h-quinazolin-4-ones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3615/77A Expired GB1574042A (en) | 1976-01-29 | 1977-01-28 | 3-(3-(3-hydroxypiperid-2-yl) acetonyl)-3h-quinazolin-4-ones |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4252947A (forum.php) |
| JP (1) | JPS5293780A (forum.php) |
| BE (1) | BE850862A (forum.php) |
| CA (1) | CA1091670A (forum.php) |
| CH (1) | CH620211A5 (forum.php) |
| DE (1) | DE2703652A1 (forum.php) |
| DK (1) | DK144822C (forum.php) |
| FR (1) | FR2339402A1 (forum.php) |
| GB (2) | GB1574043A (forum.php) |
| IE (2) | IE44861B1 (forum.php) |
| IT (1) | IT1083465B (forum.php) |
| LU (1) | LU76662A1 (forum.php) |
| NL (1) | NL7700899A (forum.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4364928A (en) * | 1979-10-23 | 1982-12-21 | Roussel-Uclaf | Novel salts of ion exchange resins of the acid type |
| US4762838A (en) * | 1985-08-30 | 1988-08-09 | Pfizer Inc. | Quinazolin-4(3H)-one derivatives as anticoccidial agents |
| US4849518A (en) * | 1987-06-22 | 1989-07-18 | Pfizer Inc. | Quinazolin-4(3H)-one derivatives as anticoccidial agents |
| US4920224A (en) * | 1988-03-24 | 1990-04-24 | Pfizer Inc. | Quinazolin-4(3H)-one derivatives as anticoccidial agents |
| DE102004058083A1 (de) * | 2004-12-01 | 2006-06-08 | Röhm GmbH & Co. KG | Gedeckt eingefärbte, infrarotreflektierende Kunststoffformmasse |
| US20080255165A1 (en) * | 2005-02-23 | 2008-10-16 | Mordechai Erez | Pharmaceutical Compositions of the Isolated D-Enantiomer of the Quinazolinone Derivative Halofuginone |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2775597A (en) * | 1954-02-12 | 1956-12-25 | American Cyanamid Co | Method for preparing quinazolone intermediates |
| US3320124A (en) * | 1964-07-20 | 1967-05-16 | American Cyanamid Co | Method for treating coccidiosis with quinazolinones |
| US3336327A (en) * | 1964-07-20 | 1967-08-15 | American Cyanamid Co | Lower alkoxy pyridyl acetones |
| DE1445551A1 (de) * | 1964-12-10 | 1969-05-22 | Boheringer Mannheim Gmbh | Verfahren zur Herstellung neuer,basisch substituierter Xanthen-9-o1-9-carbonsaeureester und deren Salzen |
-
1976
- 1976-01-29 FR FR7602413A patent/FR2339402A1/fr active Granted
-
1977
- 1977-01-26 US US05/762,503 patent/US4252947A/en not_active Expired - Lifetime
- 1977-01-27 IT IT47820/77A patent/IT1083465B/it active
- 1977-01-28 BE BE174471A patent/BE850862A/xx not_active IP Right Cessation
- 1977-01-28 JP JP792177A patent/JPS5293780A/ja active Pending
- 1977-01-28 CH CH110277A patent/CH620211A5/fr not_active IP Right Cessation
- 1977-01-28 CA CA270,787A patent/CA1091670A/fr not_active Expired
- 1977-01-28 GB GB26168/79A patent/GB1574043A/en not_active Expired
- 1977-01-28 GB GB3615/77A patent/GB1574042A/en not_active Expired
- 1977-01-28 LU LU76662A patent/LU76662A1/xx unknown
- 1977-01-28 DK DK36277A patent/DK144822C/da not_active IP Right Cessation
- 1977-01-28 NL NL7700899A patent/NL7700899A/xx active Search and Examination
- 1977-01-28 DE DE19772703652 patent/DE2703652A1/de active Granted
- 1977-01-31 IE IE2734/81A patent/IE44861B1/en not_active IP Right Cessation
- 1977-01-31 IE IE197/77A patent/IE44860B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| LU76662A1 (forum.php) | 1977-08-03 |
| DE2703652C2 (forum.php) | 1988-01-21 |
| DK36277A (da) | 1977-07-30 |
| DK144822B (da) | 1982-06-14 |
| IE44861L (en) | 1977-07-29 |
| CH620211A5 (forum.php) | 1980-11-14 |
| DE2703652A1 (de) | 1977-08-04 |
| IE44860L (en) | 1978-07-29 |
| BE850862A (fr) | 1977-07-28 |
| DK144822C (da) | 1982-11-01 |
| CA1091670A (fr) | 1980-12-16 |
| US4252947A (en) | 1981-02-24 |
| FR2339402A1 (fr) | 1977-08-26 |
| IE44860B1 (en) | 1982-04-21 |
| NL7700899A (nl) | 1977-08-02 |
| IE44861B1 (en) | 1982-04-21 |
| GB1574042A (en) | 1980-09-03 |
| FR2339402B1 (forum.php) | 1982-07-30 |
| IT1083465B (it) | 1985-05-21 |
| JPS5293780A (en) | 1977-08-06 |
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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 |
Effective date: 19940128 |