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EP0179959A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Conjugates of leukotrienes with proteins

Assignee: Merck Frosst Canada and Co
•
Filing: 1984-11-02
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Granted: —
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Expires: 2004-11-02
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Abstract

Abstract Leukotrienes B 4 , C 4 , D 4 and E 4 are conjugated with various proteins, viz. Bovine Serum Albumin, Hemocyanin from Giant Keyhole Limpets, human serum albumin, tetanus antigen, diphtheriae toxoid and CRM 197 using 1,5-difluoro-2,4-dinitrobenzene or 6-N-maleimido(C 2-8 alkanoic acid)-chloride as coupling agent. These conjugates are useful as reagents in a newly developed immunoassay for leukotrienes, as well as having potential utility as chemical immunotherapeutic agents in the treatment of various allergic and chronic inflammatory diseases of the skin, lung, and airways, including asthma, allergic rhinitis, rheumatoid arthritis, and skin diseases such as psoriasis and eczema. They may be made into pharmaceutical compositions. Certain novel intermediate compounds are also provided.

Inventors

  • 👤 Edward C. Hayes
  • 👤 Joshua Rokach
  • 👤 Robert N. Young

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-06 20:22
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/0606; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/62; A61K47/64; A61K47/643; C07C; C07C243/00; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D207/36; C07D207/40; C07D207/416; C07D207/44; C07D207/444; C07D207/456; C07D309/00; C07D309/16; C07D309/28; C07D309/30; C07K1/00; C07K1/107; C07K1/1072; C07K1/1077; C07K14/00; C07K16/00; C07K16/18; C07K17/00; C07K17/02; C07K17/06; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; G01N33/58; G01N33/60; G01N33/88; A61K38/00

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 52 words
The conjugate compound of LTB 4 , LTC 4 , LTD 4 , or LTE 4 with either KLH, BSA, human serum albumin, tetanus antigen, diphtheriae toxoid, or CRM 197, through the coupling agent 1,5-difluoro-2,4-dinitrobenzene or a 6-N-maleimido-alkanoic acid chloride, in which the alkanoic acid contains from 2 to 8 carbon atoms.
Claim 2
Dependent Claim 52 words
The conjugate compound of LTB 4 , LTC 4 , LTD 4 , or LTE 4 with either KLH, BSA, human serum albumin, tetanus antigen, diphtheriae toxoid, or CRM 197, through the coupling agent 1,5-difluoro-2,4-dinitrobenzene or a 6-N-maleimido-alkanoic acid chloride, in which the alkanoic acid contains from 2 to 8 carbon atoms.
Claim 3
Dependent Claim 20 words
The conjugate compound of LTC 4 with either KLH or BSA, through a coupling agent as defined in Claim 1.
Claim 4
Dependent Claim 20 words
The conjugate compound of LTB 4 with either KLH or BSA, through a coupling agent as defined in Claim 1.
Claim 5
Dependent Claim 19 words
A compound as claimed in Claim 1, 2 or 3 in which the coupling agent is 6-N-maleimidohexanoic acid chloride.
Claim 6
Dependent Claim 17 words
A compound as claimed in Claim 1 for use in the therapeutic treatment of animals, particularly humans.
Claim 7
Dependent Claim 46 words
A compound as claimed in any one of Claims 1 to 4, for use in treating or preventing allergic and chronic inflammatory diseases of the skin, lung, and airways by raising antibodies to LTB 4 , LTC 4 , LTD 4 and/or L TE 4 .
Claim 8
Dependent Claim 43 words
A compound as claimed in any one of Claims 1 to 4, for use in treating or preventing asthma, allergic rhinitis, rheumatoid arthritis, psoriasis or eczema by raising antibodies to LTB 4 , LTC 4 , LTD 4 and/or L TE 4 .
Claim 9
Dependent Claim 18 words
A compound of the formula: or in which n is 0 or an integer from 1 to 10.
Claim 10
Dependent Claim 18 words
A compound of the formula: or in which n is 0 or an integer from 1 to 10.
Claim 11
Dependent Claim 18 words
A compound according to Claim 8, in which n is 0 or an integer from 2 to 10.
Claim 12
Dependent Claim 11 words
A compound according to Claim 9, in which n is 3.
Claim 13
Dependent Claim 21 words
5(S),12(R)-dihydroxy-6,14(Z)-8,10(E)-eicosatetraeonic acid delta- lactone; 5(S),12(R)-5,12-dihydroxy-6,14(Z),8,10,(E)eicosapenaeonic acid hydrazide; 5(S),12(R)-N'- [α-oxo-zeta-(2',5'-dioxo-2',5'-dihydropyrrolo)hexane] - 5,12-dihydroxy-6,14(Z),8,10(E)-eicosatetraenoic acid hydrazide; N-(3-aminopropyl)-5(S),12(R)-dihydroxy-6,14(Z)-8,10(E)-eicosatetraenoic acid amide; and N-(3-[2,4-dinitro-5-fluorophenyl] aminopropyl)-5(S),12-(R)-dihydroxy-6,14(Z)-8,10(E)-eicosatetraenoic acid amide.
Claim 14
Dependent Claim 21 words
5(S),12(R)-dihydroxy-6,14(Z)-8,10(E)-eicosatetraeonic acid delta- lactone; 5(S),12(R)-5,12-dihydroxy-6,14(Z),8,10,(E)eicosapenaeonic acid hydrazide; 5(S),12(R)-N'- [α-oxo-zeta-(2',5'-dioxo-2',5'-dihydropyrrolo)hexane] - 5,12-dihydroxy-6,14(Z),8,10(E)-eicosatetraenoic acid hydrazide; N-(3-aminopropyl)-5(S),12(R)-dihydroxy-6,14(Z)-8,10(E)-eicosatetraenoic acid amide; and N-(3-[2,4-dinitro-5-fluorophenyl] aminopropyl)-5(S),12-(R)-dihydroxy-6,14(Z)-8,10(E)-eicosatetraenoic acid amide.
Claim 15
Dependent Claim 23 words
A pharmaceutical composition containing a compound as claimed in any one of Claims 1 to 4 together with a pharmaceutical diluent or excipient.

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