EP1673362A2 - Procede de production de derives de chromane substitues en position 2, exempts d'enantiomeres - Google Patents

Procede de production de derives de chromane substitues en position 2, exempts d'enantiomeres

Info

Publication number
EP1673362A2
EP1673362A2 EP04765299A EP04765299A EP1673362A2 EP 1673362 A2 EP1673362 A2 EP 1673362A2 EP 04765299 A EP04765299 A EP 04765299A EP 04765299 A EP04765299 A EP 04765299A EP 1673362 A2 EP1673362 A2 EP 1673362A2
Authority
EP
European Patent Office
Prior art keywords
chroman
formula
carbonitrile
carboxamide
preparation
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.)
Withdrawn
Application number
EP04765299A
Other languages
German (de)
English (en)
Inventor
Ralf Di Devant
Heinz-Hermann Bokel
Helmut Reubold
Herbert Pflug
Ralf Knierieme
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP1673362A2 publication Critical patent/EP1673362A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/66—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

Definitions

  • a unbranched or branched alkyl with 1-10 C atoms, in which one or two CH groups are replaced by O or S atoms and / or by -CH CH groups and / or 1-7 H atoms by F.
  • Ar can be unsaturated, partially or completely saturated, unsubstituted or mono- or polynuclear mono- or polynuclear homo- or heterocyclic system with the heteroatoms O, H, S and Hai F, Cl, substituted by shark, A, OA or NA 2 , Br or I means, characterized in that a corresponding (R) ⁇ or (S) -Chroman- 2-carboxylic acid ester of the formula IV
  • R 2 means OA or NA 2 , where A has the meaning given above and below.
  • A means alkyl, is unbranched (linear) or branched, and has 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.
  • A is preferably methyl, furthermore ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, furthermore also pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-, 2-,
  • the reaction temperature for the reactions described above is between about -10 ° C and 200 ° C, but usually between -10 ° C and 100 ° C, depending on the conditions used.
  • the reaction time is between a few seconds and several days, preferably between 1 minute and 24 hours.
  • condition used are understood to mean the type and amount of solvent, the type and amount of reagents, the reaction time, the reaction temperature and further details of the reaction, such as, for example, the stirrer speed or the other nature of the reaction vessel.
  • substitution pattern of the starting materials is also important for the course of the reaction and is therefore one of the "conditions used”.
  • the end of the reactions according to the invention is determined by suitable analysis methods, e.g. B. thin layer chromatography or HPLC, determined and interrupted the respective implementation.
  • suitable analysis methods e.g. B. thin layer chromatography or HPLC, determined and interrupted the respective implementation.
  • workup steps such. B. water or acid addition to the reaction mixture and extraction, the products and intermediates according to the invention can be obtained after removal of the solvent. It may be advantageous to connect a distillation or crystallization to further purify the product.
  • An enantiomerically pure chroman-2-carboxylic acid ester is dissolved in a suitable solvent such as e.g. Dissolved methanol, passed ammonia gas through this solution or added an aqueous ammonia solution.
  • a suitable solvent such as e.g. Dissolved methanol
  • the carboxamide separated from the reaction mixture is dissolved in a second solvent, for example toluene, and a dehydrating agent such as thionyl chloride is added.
  • the carbonitrile obtained is dissolved in a further solvent, for example methanolic ammonia, and hydrogenated, for example on a solid phase catalyst such as Raney nickel, to give the 2-aminomethylchroman according to the invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un procédé pour produire des dérivés de chromane substitués en position 2, exempts d'énantiomères, à partir des esters d'acide chroman-2-carboxylique exempts d'énantiomères correspondants.
EP04765299A 2003-10-16 2004-09-16 Procede de production de derives de chromane substitues en position 2, exempts d'enantiomeres Withdrawn EP1673362A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2003148257 DE10348257A1 (de) 2003-10-16 2003-10-16 Verfahren zur Herstellung von enantiomereneinen in 2-Position substituierten Chromanderivaten
PCT/EP2004/010399 WO2005037817A2 (fr) 2003-10-16 2004-09-16 Procede de production de derives de chromane substitues en position 2, exempts d'enantiomeres

Publications (1)

Publication Number Publication Date
EP1673362A2 true EP1673362A2 (fr) 2006-06-28

Family

ID=34442025

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04765299A Withdrawn EP1673362A2 (fr) 2003-10-16 2004-09-16 Procede de production de derives de chromane substitues en position 2, exempts d'enantiomeres

Country Status (3)

Country Link
EP (1) EP1673362A2 (fr)
DE (1) DE10348257A1 (fr)
WO (1) WO2005037817A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PE20061297A1 (es) 2005-04-22 2006-12-24 Wyeth Corp Compuestos derivados de cromano y cromeno moduladores del receptor de serotonina 5-ht2c

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0115142B1 (fr) * 1982-12-23 1986-11-05 Ici Americas Inc. Composés chromaniques
US6469031B1 (en) * 1998-12-18 2002-10-22 Bayer Corporation Carboxyl substituted chroman derivatives useful as beta 3 adrenoreceptor agonists
AR035605A1 (es) * 2000-12-11 2004-06-16 Bayer Corp Derivados de aminometil cromano di-sustituidos, un metodo para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la manufactura de medicamentos utiles como agonistas beta-3-adreno-receptores

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005037817A3 *

Also Published As

Publication number Publication date
DE10348257A1 (de) 2005-05-25
WO2005037817A2 (fr) 2005-04-28
WO2005037817A3 (fr) 2005-06-23

Similar Documents

Publication Publication Date Title
EP1678119B1 (fr) Procede de production d'esters d'acide 2-dihalogeno-acyl-3-amino-acrylique et d'esters d'acide 3-dihalogeno-methyl-pyrazol-4-carboxylique
DE69710052T2 (de) Verfahren zur herstellung von zwischenprodukten für pestizide
EP0380712B1 (fr) Procédé de préparation de dérivés de l'acide 2,6-dichlorodiphénylaminoacétique
CH617934A5 (fr)
EP1067129B1 (fr) La racemisation de la R,S-dioxo-benzylpyrrolopipéridine
EP1673362A2 (fr) Procede de production de derives de chromane substitues en position 2, exempts d'enantiomeres
DE69703115T2 (de) Zwischenprodukte um 2-imidazolin-5onederivate herzustellen.
DE69623117T2 (de) Verfahren zur herstellung von 4-hydroxy-2-pyrrolidon
DE60010090T2 (de) Verfahren zur cis-selektiven katalytischen hydrierung von cyclohexylidenaminen
EP0923534B1 (fr) Procede de preparation d'amines phenethyliques racemiques
DE2804263C3 (de) Verfahren zur Herstellung von Indolin-Derivaten
EP0324336B2 (fr) Procédé pour la preparation de 3-cyano-4-aryl-pyrroles
EP3088383A1 (fr) Synthèse optimisée de prégabaline et 4-acides aminobutyriques selon un procédé de fabrication amélioré de nitroalcènes conjugués
EP1615891B1 (fr) Procede pour produire des aldehydes de nicotine
JP5487692B2 (ja) 複素環骨格を有する化合物および該化合物を不斉触媒として用いる光学活性化合物の製造方法
DE2720915C2 (de) N↓1↓-Acyl-2-hydroxy-1,3-diaminopropane und Arzneimittel mit diesen Verbindungen als Wirkstoff
DE19947953A1 (de) Verfahren zur selektiven Spaltung cyclischer Carbonsäureanhydride
EP1232151A1 (fr) Procede de preparation de benzofuranonoximes
DE3815046A1 (de) 3-chlor-2-methylphenethylaminoderivate
AT500910B1 (de) Verfahren zur herstellung von beta-hydroxynitroverbindungen
DE60224732T2 (de) Verfahren zur herstellung der enantiomeren formen von 2- substituierten 2-(2,5-dioxoimidazolidin-1-yl)essigsäurederivaten
DE2264663C3 (de) Ungesättigte Sulfoxyde und Verfahren zu ihrer Herstellung
DE3607993A1 (de) Verfahren zur herstellung von diaziridinen und produkte daraus
KR20230040136A (ko) 프롤린 이소티오우로늄 염 화합물 및 이를 이용한 베타 하이드록시 카보닐 화합물의 제조방법
EP1299394A1 (fr) Procede de preparation de (+)-biotine

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20060217

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: LT LV

RAX Requested extension states of the european patent have changed

Extension state: LV

Payment date: 20060217

Extension state: LT

Payment date: 20060217

17Q First examination report despatched

Effective date: 20070704

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20071115