CA2324921A1 - Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections - Google Patents

Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections Download PDF

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Publication number
CA2324921A1
CA2324921A1 CA002324921A CA2324921A CA2324921A1 CA 2324921 A1 CA2324921 A1 CA 2324921A1 CA 002324921 A CA002324921 A CA 002324921A CA 2324921 A CA2324921 A CA 2324921A CA 2324921 A1 CA2324921 A1 CA 2324921A1
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CA
Canada
Prior art keywords
12alkyl
mono
aryl
amino
phenyl
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.)
Granted
Application number
CA002324921A
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French (fr)
Other versions
CA2324921C (en
Inventor
Frederik Frans Desire Daeyaert
Bart De Corte
Marc Rene De Jonge
Jan Heeres
Chih Yung Ho
Paul Adriaan Jan Janssen
Robert W. Kavash
Lucien Maria Henricus Koymans
Michael Joseph Kukla
Donald William Ludovici
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.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica N.V.
Frederik Frans Desire Daeyaert
Bart De Corte
Marc Rene De Jonge
Jan Heeres
Chih Yung Ho
Paul Adriaan Jan Janssen
Robert W. Kavash
Lucien Maria Henricus Koymans
Michael Joseph Kukla
Donald William Ludovici
Janssen Pharmaceutica Inc.
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 Janssen Pharmaceutica N.V., Frederik Frans Desire Daeyaert, Bart De Corte, Marc Rene De Jonge, Jan Heeres, Chih Yung Ho, Paul Adriaan Jan Janssen, Robert W. Kavash, Lucien Maria Henricus Koymans, Michael Joseph Kukla, Donald William Ludovici, Janssen Pharmaceutica Inc. filed Critical Janssen Pharmaceutica N.V.
Publication of CA2324921A1 publication Critical patent/CA2324921A1/en
Application granted granted Critical
Publication of CA2324921C publication Critical patent/CA2324921C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/66—Derivatives of melamine in which a hetero atom is directly attached to a nitrogen atom of melamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

This invention concerns the use of the compounds of formula (I) the N-oxides, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein A is CH, CR4 or N; n is 0, 1, 2, 3 or 4; R1 and R2 are each independently selected from hydrogen, hydroxy, C1-12alkyl, C1-12alkyloxy, C1-12alkylcarbonyl, C1-12alkyloxycarbonyl, aryl, amino, mono-or di(C1-12alkyl)amino, mono- or di(C1-12alkyl)aminocarbonyl wherein each of the aforementioned C1-12alkyl groups may optionally and each individually be substituted; or R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-12alkyl)aminoC1-4alkylidene; R3 is hydrogen, aryl, C1-6alkylcarbonyl, optionally substituted C1-6alkyl; and each R4 independently is hydroxy, halo, C1-6alky1, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy; L is -X-R5 or -X-Alk-R6;
wherein R5 and R6 each independently are indanyl, indolyl or phenyl; each of said indanyl, indolyl or phenyl may be substituted; and X is -NR3-, -NH-NH-, -N-N-, -O-, -S-, -S(-O)- or -S(-O)2-; aryl is optionally substituted phenyl; Het is an optionally substituted aliphatic or aromatic heterocyclic radical; for the manufacture of a medicine for the treatment of subjects suffering from HIV (Human Immunodeficiency Virus) infection. It further relates to new compounds being a subgroup of the compounds of formula (I), their preparation and pharmaceutical compositions comprising them.
CA002324921A 1998-03-27 1999-03-24 Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections Expired - Fee Related CA2324921C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US7963398P 1998-03-27 1998-03-27
US60/079,633 1998-03-27
EP98201589A EP0945447A1 (en) 1998-03-27 1998-05-14 Trisubstituted 1,3,5-triazine derivatives for treatment of HIV infections
EP98201589.3 1998-05-14
PCT/EP1999/002044 WO1999050256A1 (en) 1998-03-27 1999-03-24 Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections

Publications (2)

Publication Number Publication Date
CA2324921A1 true CA2324921A1 (en) 1999-10-07
CA2324921C CA2324921C (en) 2009-05-12

Family

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CA002324921A Expired - Fee Related CA2324921C (en) 1998-03-27 1999-03-24 Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections

Country Status (33)

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US (3) US6150360A (en)
EP (2) EP0945447A1 (en)
JP (1) JP2002511390A (en)
KR (1) KR100593396B1 (en)
CN (1) CN1157386C (en)
AP (1) AP1475A (en)
AR (1) AR018169A1 (en)
AT (1) ATE295355T1 (en)
AU (1) AU758624C (en)
BG (1) BG64903B1 (en)
BR (1) BR9909197A (en)
CA (1) CA2324921C (en)
DE (1) DE69925256T2 (en)
DK (1) DK1066269T3 (en)
EA (1) EA004540B1 (en)
EE (1) EE200000535A (en)
ES (1) ES2243056T3 (en)
HK (1) HK1032394A1 (en)
HR (1) HRP20000621A2 (en)
HU (1) HUP0101372A3 (en)
ID (1) ID26043A (en)
IL (1) IL138670A (en)
NO (1) NO317425B1 (en)
NZ (1) NZ506787A (en)
OA (1) OA11493A (en)
PL (1) PL194660B1 (en)
PT (1) PT1066269E (en)
SI (1) SI1066269T1 (en)
SK (1) SK14052000A3 (en)
TR (1) TR200002761T2 (en)
TW (1) TW570917B (en)
WO (1) WO1999050256A1 (en)
ZA (1) ZA200006042B (en)

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DE69925256D1 (en) 2005-06-16
KR100593396B1 (en) 2006-06-28
EE200000535A (en) 2002-04-15
IL138670A (en) 2005-12-18
HK1032394A1 (en) 2001-07-20
ES2243056T3 (en) 2005-11-16
ID26043A (en) 2000-11-16
DK1066269T3 (en) 2005-09-05
BG64903B1 (en) 2006-08-31
CA2324921C (en) 2009-05-12
PT1066269E (en) 2005-09-30
NO20004809L (en) 2000-11-24
WO1999050256A1 (en) 1999-10-07
ATE295355T1 (en) 2005-05-15
EP1066269B1 (en) 2005-05-11
AU3599799A (en) 1999-10-18
AU758624C (en) 2004-03-11
NO317425B1 (en) 2004-10-25
NZ506787A (en) 2003-02-28
US6774235B2 (en) 2004-08-10
KR20010034270A (en) 2001-04-25
CN1295566A (en) 2001-05-16
NO20004809D0 (en) 2000-09-26
AU758624B2 (en) 2003-03-27
US20020115668A1 (en) 2002-08-22
JP2002511390A (en) 2002-04-16
US6150360A (en) 2000-11-21
PL194660B1 (en) 2007-06-29
TR200002761T2 (en) 2001-01-22
CN1157386C (en) 2004-07-14
HUP0101372A3 (en) 2003-02-28
US6372729B1 (en) 2002-04-16
AP1475A (en) 2005-10-03
EA004540B1 (en) 2004-06-24
EP1066269A1 (en) 2001-01-10
BR9909197A (en) 2000-12-05
BG104716A (en) 2001-04-30
EA200000993A1 (en) 2001-04-23
SI1066269T1 (en) 2005-10-31
DE69925256T2 (en) 2006-02-23
AP2000001913A0 (en) 2000-09-30
EP0945447A1 (en) 1999-09-29
TW570917B (en) 2004-01-11
HRP20000621A2 (en) 2001-04-30
OA11493A (en) 2004-05-07
SK14052000A3 (en) 2001-06-11
PL343195A1 (en) 2001-07-30
HUP0101372A2 (en) 2001-10-28
ZA200006042B (en) 2001-10-26
AR018169A1 (en) 2001-10-31

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