PE20010702A1 - PROCESS FOR THE PREPARATION OF ARYLOXYPROPANOLAMINES - Google Patents
PROCESS FOR THE PREPARATION OF ARYLOXYPROPANOLAMINESInfo
- Publication number
- PE20010702A1 PE20010702A1 PE2000001222A PE0012222000A PE20010702A1 PE 20010702 A1 PE20010702 A1 PE 20010702A1 PE 2000001222 A PE2000001222 A PE 2000001222A PE 0012222000 A PE0012222000 A PE 0012222000A PE 20010702 A1 PE20010702 A1 PE 20010702A1
- Authority
- PE
- Peru
- Prior art keywords
- aryloxypropanolamine
- ethanol
- ester
- acid
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-HQMMCQRPSA-N Ethanol-14C Chemical compound C[14CH2]O LFQSCWFLJHTTHZ-HQMMCQRPSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002118 epoxides Chemical class 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 abstract 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000002778 food additive Substances 0.000 abstract 1
- 235000013373 food additive Nutrition 0.000 abstract 1
- 235000020997 lean meat Nutrition 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/465—Nicotine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
SE REFIERE A UN METODO PARA PREPARAR UN ESTER DE ARILOXIPROPANOLAMINA DE FORMULA I, DONDE R1 ES ARILO, R2 ES ALQUILO C1-C6, ARALQUILO C7-C9; QUE COMPRENDE REACCIONAR UN EPOXIDO DE FROMULA II, R1 ES UN GRUPO A, B, DC, ENTRE OTROS; A1 Y A2 SON C, N; A3, A4 SON O, S, NH, CH2, ENTRE OTROS; n ES 1-2; R2 ES METILO, ETILO; CON UNA AMINA DE FROMULA III; REACCIONAR EL ESTER DE ARILOXIPROPANOLAMINA CON UN ACIDO (ACIDO 4-HIDROXIBENZOICO, ACIDO FTALICO, ACIDO 2-HIDROXINICOTINICO, ACIDO GLICOLICO, ENTRE OTROS); PARA FORMAR LA SAL DE AMONIO CUATERNARIO CON EL ESTER DE ARILOXIPROPANOLAMINA; CRISTALIZAR LA SAL DE AMONIO CUATERNARIO A PARTIR DE ETANOL, UNA MEZCLA DE CLOROBENCENO:ETANOL, UNA MEZCLA DE ANISOL:ETANOL, UNA MEZCLA DE DICLOROMETANO:ETANOL; UTILIZANDO DE 0,9 A 2 EQUIVALENTES DE AMINA EN RELACION AL EPOXIDO; TAMBIEN SE REFIERE A LA PREPARACION DE LA AMINA REACCIONANDO UN ESTER DE 2-HALOPIRIDA Y UNA SAL DE FENOXIDO DE UN ALQUILAMINOFENOL. LOS ESTERES DE ARILOXIPROPANOLAMINA SE PUEDEN CONVERTIR EN AMIDAS DE ARILOXIPROPANOLAMINAS QUE SON UTILES EN EL TRATAMIENTO DE LA OBESIDAD Y DIABETES TIPO II Y COMO ADITIVOS ALIMENTARIOS PARA GANADO PARA PRODUCIR CARNE MAGRAREFERS TO A METHOD TO PREPARE AN ESTER OF ARYLOXYPROPANOLAMINE OF FORMULA I, WHERE R1 IS ARYL, R2 IS C1-C6 ALKYL, C7-C9 ARALKYL; WHICH INCLUDES REACTING AN EPOXIDE FROM FROMULA II, R1 IS A GROUP A, B, DC, AMONG OTHERS; A1 AND A2 ARE C, N; A3, A4 ARE O, S, NH, CH2, AMONG OTHERS; n IS 1-2; R2 IS METHYL, ETHYL; WITH AN AMINE FROM FROMULA III; REACT THE ARYLOXYPROPANOLAMINE ESTER WITH AN ACID (4-HYDROXYBENZOIC ACID, PHTHALIC ACID, 2-HYDROXYNICOTINIC ACID, GLYCOLIC ACID, AMONG OTHERS); TO FORM THE QUATERNARY AMMONIUM SALT WITH THE ARYLOXYPROPANOLAMINE ESTER; CRYSTALLIZING QUATERNARY AMMONIUM SALT FROM ETHANOL, A MIXTURE OF CHLOROBENZENE: ETHANOL, A MIXTURE OF ANISOL: ETHANOL, A MIXTURE OF DICHLOROMETHANE: ETHANOL; USING 0.9 TO 2 AMINE EQUIVALENTS IN RELATION TO EPOXIDE; IT ALSO REFERS TO THE PREPARATION OF AMINE BY REACTING AN ESTER OF 2-HALOPYRIDE AND A SALT OF PHENOXIDE OF AN ALKYLAMINOPHENOL. ARYLOXYPROPANOLAMINE ESTERS CAN BE CONVERTED INTO ARYLOXYPROPANOLAMIN AMIDES THAT ARE USEFUL IN THE TREATMENT OF OBESITY AND TYPE II DIABETES AND AS FOOD ADDITIVES FOR CATTLE TO PRODUCE LEAN MEAT
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16559499P | 1999-11-15 | 1999-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20010702A1 true PE20010702A1 (en) | 2001-07-07 |
Family
ID=22599580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2000001222A PE20010702A1 (en) | 1999-11-15 | 2000-11-15 | PROCESS FOR THE PREPARATION OF ARYLOXYPROPANOLAMINES |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU1580001A (en) |
| PE (1) | PE20010702A1 (en) |
| WO (1) | WO2001036412A1 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001036390A1 (en) | 1999-11-15 | 2001-05-25 | Eli Lilly And Company | Indazolyloxy propanolamines for improving livestock production |
| US6825220B2 (en) | 2000-11-10 | 2004-11-30 | Eli Lilly And Company | 3-Substituted oxindole β 3 agonists |
| ATE340794T1 (en) | 2001-08-14 | 2006-10-15 | Lilly Co Eli | INDOLE DERIVATIVES AS BETA-3 ADRENERGIC AGONISTS FOR THE TREATMENT OF TYPE 2 DIABETES |
| JP2005507872A (en) | 2001-08-14 | 2005-03-24 | イーライ・リリー・アンド・カンパニー | 3-Substituted oxindole β3 agonist |
| EP1448561B1 (en) | 2001-11-20 | 2008-02-20 | Eli Lilly And Company | Beta 3 adrenergic agonists |
| ES2242890T3 (en) | 2001-11-20 | 2005-11-16 | Eli Lilly And Company | BETA 3 AGONISTS OF OXINDOL 3-REPLACED. |
| WO2003059348A1 (en) | 2002-01-11 | 2003-07-24 | Eli Lilly And Company | 2-oxo-benzimidazolyl substituted ethanolamine derivatives and their use as beta3 agonists |
| AU2013327689B2 (en) | 2012-10-02 | 2016-03-17 | Eli Lilly And Company | Methods for improving chicken production |
| CN115611752A (en) * | 2022-10-21 | 2023-01-17 | 江苏天和制药有限公司 | Synthetic refining method of lubabylon intermediate |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH624395A5 (en) * | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
| DE2719562C2 (en) * | 1976-05-08 | 1986-05-07 | Otsuka Pharmaceutical Co. Ltd., Tokio/Tokyo | 3, 4-Dihydrocarbostyril derivatives, processes for their preparation and pharmaceuticals containing them |
| CH607585A5 (en) * | 1976-10-05 | 1978-09-15 | Ciba Geigy Ag | Process for the preparation of 2-[3'-(2-(3,4-dimethoxy-phenyl)ethylamino)-2'-hydroxypropoxy]-3-cyanop yridine |
| DE2830211A1 (en) * | 1977-07-21 | 1979-02-01 | Sandoz Ag | SUBSTITUTED INDOL DERIVATIVES, THEIR PRODUCTION AND USE |
| KR19990045727A (en) * | 1995-09-21 | 1999-06-25 | 피터 지. 스트링거 | Selective β3 Adrenaline Agonists |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| ES2171839T3 (en) * | 1996-09-05 | 2002-09-16 | Lilly Co Eli | CARBAZOL ANALOGS AS BETA3 SELECTIVE ADRENERGIC AGONISTS. |
| US5808080A (en) * | 1996-09-05 | 1998-09-15 | Eli Lilly And Company | Selective β3 adrenergic agonists |
| CO5011072A1 (en) * | 1997-12-05 | 2001-02-28 | Lilly Co Eli | ETANOLAMINAS PIRAZINIL SUBSTITUTED AS AGFONISTS OF THE RECEPTORS |
-
2000
- 2000-11-13 WO PCT/US2000/030128 patent/WO2001036412A1/en not_active Ceased
- 2000-11-13 AU AU15800/01A patent/AU1580001A/en not_active Abandoned
- 2000-11-15 PE PE2000001222A patent/PE20010702A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001036412A1 (en) | 2001-05-25 |
| AU1580001A (en) | 2001-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |