WO1999065864A3 - Geminally substituted amines - Google Patents

Geminally substituted amines Download PDF

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Publication number
WO1999065864A3
WO1999065864A3 PCT/EP1999/004258 EP9904258W WO9965864A3 WO 1999065864 A3 WO1999065864 A3 WO 1999065864A3 EP 9904258 W EP9904258 W EP 9904258W WO 9965864 A3 WO9965864 A3 WO 9965864A3
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
aryl
cycloalkyl
alkinyl
cycloalkenyl
Prior art date
Application number
PCT/EP1999/004258
Other languages
German (de)
French (fr)
Other versions
WO1999065864A2 (en
Inventor
Herwig Buchholz
Urs Welz-Biermann
Original Assignee
Merck Patent Gmbh
Herwig Buchholz
Urs Welz-Biermann
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
Priority claimed from DE19827163A external-priority patent/DE19827163A1/en
Priority claimed from DE19827161A external-priority patent/DE19827161A1/en
Priority claimed from DE19827164A external-priority patent/DE19827164A1/en
Priority claimed from DE19827165A external-priority patent/DE19827165A1/en
Priority claimed from DE19827166A external-priority patent/DE19827166A1/en
Priority claimed from DE19844194A external-priority patent/DE19844194A1/en
Application filed by Merck Patent Gmbh, Herwig Buchholz, Urs Welz-Biermann filed Critical Merck Patent Gmbh
Publication of WO1999065864A2 publication Critical patent/WO1999065864A2/en
Publication of WO1999065864A3 publication Critical patent/WO1999065864A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/023—Preparation; Separation; Stabilisation; Use of additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
    • B01J31/0212—Alkoxylates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0274—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 containing silicon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/66—Preparation of compounds containing amino groups bound to a carbon skeleton from or via metallo-organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to an amine of the general formula (I) in which R?1 and R2¿ may be the same or different and represent each independently substituted or non-substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkinyl, aryl or trialkylsilyl. R?1 and R2¿ can also form together with the nitrogen atom to which they are bound a substituted or non-substituted cycloalkyl ring which may contain, together with the nitrogen atom, at least one other heteroatom selected from the group comprising nitrogen, oxygen and sulphur. R3 is selected from the group comprising hydrogen and methyl optionally substituted with 1 to 3 fluorine atoms, while R?4 and R5¿ may be the same or different and represent each independently alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkinyl or substituted or non-substituted aryl. R?4 and R5¿ may also represent alkyl substituted with a substituted or non-substituted aryl, cycloalkyl, alkenyl, cycloalkenyl or alkinyl, with the proviso that at least one of the R?4 and R5¿ radicals comprises an aryl. This invention also relates to a salt thereof.
PCT/EP1999/004258 1998-06-18 1999-06-18 Geminally substituted amines WO1999065864A2 (en)

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
DE19827163A DE19827163A1 (en) 1998-06-18 1998-06-18 Process for the catalytic, asymmetrical disubstitution of carboxamides with 2 different Grignard reagents
DE19827163.8 1998-06-18
DE19827161.1 1998-06-18
DE19827166.2 1998-06-18
DE19827161A DE19827161A1 (en) 1998-06-18 1998-06-18 Process for the catalytic, symmetrical disubstitution of carboxamides with Grignard reagents
DE19827164.6 1998-06-18
DE19827167.0 1998-06-18
DE19827164A DE19827164A1 (en) 1998-06-18 1998-06-18 Catalytic titanium (IV) oxide mediated geminal symmetrical dialkylation of carboxamides
DE19827167 1998-06-18
DE19827165A DE19827165A1 (en) 1998-06-18 1998-06-18 Catalytic titanium (IV) oxide-mediated, unsymmetrical dialkylation of carboxamides
DE19827165.4 1998-06-18
DE19827166A DE19827166A1 (en) 1998-06-18 1998-06-18 Process for the catalytic disubstitution of carboxamides with at least one Grignard reagent
DE19844194.0 1998-09-26
DE19844194A DE19844194A1 (en) 1998-06-18 1998-09-26 Process for the symmetrical or asymmetrical disubstitution of carboxamides with organotitanates and Grignard reagents

Publications (2)

Publication Number Publication Date
WO1999065864A2 WO1999065864A2 (en) 1999-12-23
WO1999065864A3 true WO1999065864A3 (en) 2003-05-22

Family

ID=27561759

Family Applications (4)

Application Number Title Priority Date Filing Date
PCT/EP1999/004256 WO1999065318A2 (en) 1998-06-18 1999-06-18 Geminally substituted amines
PCT/EP1999/004257 WO1999065863A1 (en) 1998-06-18 1999-06-18 Method for producing combinatory amine libraries
PCT/EP1999/004258 WO1999065864A2 (en) 1998-06-18 1999-06-18 Geminally substituted amines
PCT/EP1999/004255 WO1999065855A2 (en) 1998-06-18 1999-06-18 Combinatorial libraries of geminally substituted amines

Family Applications Before (2)

Application Number Title Priority Date Filing Date
PCT/EP1999/004256 WO1999065318A2 (en) 1998-06-18 1999-06-18 Geminally substituted amines
PCT/EP1999/004257 WO1999065863A1 (en) 1998-06-18 1999-06-18 Method for producing combinatory amine libraries

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/004255 WO1999065855A2 (en) 1998-06-18 1999-06-18 Combinatorial libraries of geminally substituted amines

Country Status (3)

Country Link
EP (2) EP1088029A1 (en)
JP (2) JP2002518366A (en)
WO (4) WO1999065318A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19960377A1 (en) * 1999-12-14 2001-06-21 Merck Patent Gmbh Process for the preparation of combinatorial amine libraries
DE19961372A1 (en) * 1999-12-17 2001-06-21 Merck Patent Gmbh Process for the preparation of combinatorial libraries of aryl substituted amines
RU2617641C2 (en) * 2010-09-20 2017-04-25 Сирна Терапьютикс,Инк. Novel low-molecular cationic lipids for delivery of oligonucleotides
GB201208775D0 (en) * 2012-05-18 2012-07-04 Uni I Oslo Chemical compounds

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB807835A (en) * 1955-07-01 1959-01-21 Thomae Gmbh Dr K New tertiary amines and their salts and process for their preparation
GB921943A (en) * 1959-11-25 1963-03-27 Lilly Co Eli Anti-hypertensive compositions
US4020059A (en) * 1975-06-02 1977-04-26 Nippon Shokubai Kagaku Kogyo Co., Ltd. Process for preparing tertiary amines
DE2725245A1 (en) * 1976-06-03 1977-12-15 Labaz METHYLAMINE DERIVATIVES, THE PROCESS FOR THEIR PRODUCTION AND THE PHARMACEUTICAL OR VETERINARY MEDICAL COMPOSITIONS THEREOF
DE2657476A1 (en) * 1976-12-18 1978-06-22 Basf Ag MORPHOLINE DERIVATIVES
WO1998000398A1 (en) * 1996-06-28 1998-01-08 University Of Southern California Method for the synthesis of amines and amino acids with organoboron derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2207137A1 (en) * 1996-06-14 1997-12-14 James Erwin Fritz Scavenger assisted combinatorial process for preparing libraries of secondary amine compounds

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB807835A (en) * 1955-07-01 1959-01-21 Thomae Gmbh Dr K New tertiary amines and their salts and process for their preparation
GB921943A (en) * 1959-11-25 1963-03-27 Lilly Co Eli Anti-hypertensive compositions
US4020059A (en) * 1975-06-02 1977-04-26 Nippon Shokubai Kagaku Kogyo Co., Ltd. Process for preparing tertiary amines
DE2725245A1 (en) * 1976-06-03 1977-12-15 Labaz METHYLAMINE DERIVATIVES, THE PROCESS FOR THEIR PRODUCTION AND THE PHARMACEUTICAL OR VETERINARY MEDICAL COMPOSITIONS THEREOF
DE2657476A1 (en) * 1976-12-18 1978-06-22 Basf Ag MORPHOLINE DERIVATIVES
WO1998000398A1 (en) * 1996-06-28 1998-01-08 University Of Southern California Method for the synthesis of amines and amino acids with organoboron derivatives

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
"BEILSTEINS HANDBUCH DER ORGANISCHEN CHEMIE, vierte Auflage, drittes Ergänzungswerk, Band IV, erster Teil, S. 308, 428", 1962, SPRINGER-VERLAG, BERLIN . GÖTTINGEN . HEIDELBERG, XP002118210 *
"BEILSTEINS HANDBUCH DER ORGANISCHEN CHEMIE, vierte Auflage, drittes Ergänzungswerk, Band XII, vierter Teil, S. 2223-2224", 1972, SPRINGER-VERLAG, BERLIN . HEIDELBERG . NEW YORK, XP002118212 *
"BEILSTEINS HANDBUCH DER ORGANISCHEN CHEMIE, vierte Auflage, drittes und viertes Ergänzungswerk, Bd 20, erster Teil, S. 316", 1977, SPRINGER-VERLAG, BERLIN . HEIDELBERG . NEW YORK, XP002117681 *
"BEILSTEINS HANDBUCH DER ORGANISCHEN CHEMIE, vierte Auflage, viertes Ergänzungswerk, Band IV, erster Teil, S. 689, 745", 1977, SPRINGER-VERLAG, BERLIN . HEIDELBERG . NEW YORK, XP002118211 *
"BEILSTEINS HANDBUCH DER ORGANISCHEN CHEMIE, vierte Auflage, viertes Ergänzungswerk, Band XII, vierter Teil, S. 2182", 1984, SPRINGER-VERLAG, BERLIN . HEIDELBERG . NEW YORK . TOKYO, XP002118213 *
"HOUBEN-WEYL, METHODEN DER ORGANISCHEN CHEMIE, vol. XI/1, S. 820-823", 1957, GEORG THIEME VERLAG, STUTTGART, DE, XP002117680 *
AN. QUIM., vol. 69, no. 9-10, 1973, pages 1047 - 1054 *
CHEMICAL ABSTRACTS, vol. 80, no. 21, 27 May 1974, Columbus, Ohio, US; abstract no. 120423p, IBANEZ-PANIELLO: "Synthesis of dibenzylamine derivatives..." page 394; column 1; XP002118214 *
FRANK G. RIDDELL ET AL.: "Intramolecular motions.....", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2., 1996, LETCHWORTH GB, pages 493 - 504, XP002118208 *
KUFFNER ET AL.: "Über hochverzeigte aliphatische Verbindungen.", MONATSHEFTE FÜR CHEMIE, vol. 82, 1951, pages 330 - 335, XP002117674 *
KUFFNER F. ET AL.: "Über hochverzweigte aliphatische Verbindungen", MONATSHEFTE FÜR CHEMIE, vol. 93, 1962, pages 499 - 475, XP002117676 *
MICHAEL B. SMITH ET AL.: "Reaction of amines with cyclopropylcarbinyl halides", JOURNAL OF ORGANIC CHEMISTRY., vol. 50, no. 24, 1985, EASTON US, pages 4815 - 4821, XP002118209 *
N. MAXIM ET AL.: "Sur la méthode de Bouveault ....", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE., vol. 5, no. 3, 1936, SOCIETE FRANCAISE DE CHIMIE. PARIS., FR, pages 1084 - 1093, XP002117677, ISSN: 0037-8968 *
R. LUKÈS ET AL.: "Die Spaltung verzweigter, optisch aktiver tertiärer basen", COLLECTION CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 24, 1959, pages 110 - 115, XP002117675 *
R. LUKÈS ET AL.: "Über die Spaltung verzweigter tertiärer Basen II.", COLLECTION CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 25, 1960, pages 461 - 464, XP002117678 *

Also Published As

Publication number Publication date
WO1999065864A2 (en) 1999-12-23
JP2003524588A (en) 2003-08-19
WO1999065318A3 (en) 2003-04-17
WO1999065863A1 (en) 1999-12-23
EP1088029A1 (en) 2001-04-04
WO1999065318A2 (en) 1999-12-23
EP1087929A1 (en) 2001-04-04
JP2002518366A (en) 2002-06-25
WO1999065855A2 (en) 1999-12-23
WO1999065855A3 (en) 2003-12-11

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