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Martin Kuehne Phones & Addresses

  • 169 Cove Rd, Burl, VT 05401 (802) 862-7303
  • Burlington, VT
  • Clear Lake, MN
  • Cambridge, VT
  • Fairfax, VT
  • 169 S Cove Rd, Burlington, VT 05401

Publications

Us Patents

Synthesis Of Vinblastine And Vincristine Type Compounds

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US Patent:
48974773, Jan 30, 1990
Filed:
Jan 26, 1988
Appl. No.:
7/148461
Inventors:
Martin Kuehne - Burlington VT
Assignee:
University of Vermont & State Agricultural College - Burlington VT
International Classification:
C07D51904
US Classification:
540478
Abstract:
A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.

Process For The Synthesis Of Vincadifformine And Related Derivatives

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US Patent:
42673305, May 12, 1981
Filed:
Aug 24, 1978
Appl. No.:
5/936454
Inventors:
Martin E. Kuehne - Burlington VT
Assignee:
Omnium Chimique Societe Anonyme - Brussels
International Classification:
C07D47114
C07D48704
US Classification:
546 51
Abstract:
This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties. A N-benzyl-tetrahydro-. gamma. -carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.

Azepino[4,5-D]Indole Derivatives And Preparation Thereof

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US Patent:
44288808, Jan 31, 1984
Filed:
Sep 29, 1982
Appl. No.:
6/426659
Inventors:
Martin E. Kuehne - Burlington VT
Assignee:
S.A. Omnichem - Louvain-la-Neuve
International Classification:
C07D48704
US Classification:
2602457
Abstract:
This invention relates to novel tetrahydroazepinoindoles used in the preparation of novel alkyl pyrrolo(2,3-d)carbazole-6-carboxylates and to addition salts thereof; and to preparation of the same by a synthesis sequence starting from a tryptamine and a 3-halopyruvate and involving a rearrangement of the reaction mixture, said rearrangement being effected by heating the reaction mixture in the presence of a base. The pyrrolo(2,3-d)carbazole final products have both antianoxic and psychotropic activities.

Preparation Of Vincadifformine

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US Patent:
41549430, May 15, 1979
Filed:
Dec 29, 1977
Appl. No.:
5/865657
Inventors:
Martin E. Kuehne - Burlington VT
Assignee:
University of Vermont - Burlington VT
International Classification:
C07D48716
US Classification:
546 51
Abstract:
The invention relates to the preparation of vincadifformine. Tetrahydro-. beta. -carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-[3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (IX). In an alternative embodiment, compound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX).

Novel Alkaloids

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US Patent:
50951092, Mar 10, 1992
Filed:
Mar 23, 1990
Appl. No.:
7/498129
Inventors:
Martin Kuehne - Burlington VT
Assignee:
University of Vermont - Burlington VT
State Agricultural College - Burlington VT
International Classification:
C07D48700
US Classification:
540479
Abstract:
Cycloalkyl and aromatic vinblastine and vincristine derivatives useful as anti-tumor agents.

Vincadifformine Synthesis Process

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US Patent:
42207746, Sep 2, 1980
Filed:
Oct 26, 1978
Appl. No.:
5/954741
Inventors:
Martin E. Kuehne - Burlington VT
Assignee:
Omnium Chimique - Brussells
International Classification:
C07D47108
US Classification:
546 51
Abstract:
The preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.

Synthesis Of Vinblastine And Vincristine Type Compounds

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US Patent:
48410454, Jun 20, 1989
Filed:
May 18, 1987
Appl. No.:
7/050807
Inventors:
Martin Kuehne - Burlington VT
Assignee:
University of Vermont & State Agricultural College - Burlington VT
International Classification:
C07D51904
C07D46100
C07D48704
US Classification:
540478
Abstract:
A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.

Modulator Agent And Use Thereof

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US Patent:
53691113, Nov 29, 1994
Filed:
Jun 19, 1992
Appl. No.:
7/900745
Inventors:
Martin E. Kuehne - Burlington VT
Linda S. Borman - Essex Junction VT
Assignee:
University of Vermont - Burlington VT
International Classification:
A61K 3144
US Classification:
514283
Abstract:
Sensitizing tumoral cells to anticancerous drugs and/or inhibiting the tumoral cells resistance to antitumoral drugs employing as a modulator agent a vinca alkaloid dimer, analog to vinblastine or vincristine, with a low cytotoxicity or devoid of cytotoxicity, comprising at least one stereoisomerism different from that of vinblastine or vincristine in the C-14', C-16' or C-20' position. Notably, the modulator agent may have the R absolute configuration in the C-16' position.
Martin E Kuehne from Burlington, VT, age ~93 Get Report