ZA200403009B - Methods and compositions of novel triazine compounds - Google Patents

Info

Publication number

ZA200403009B

ZA200403009B ZA200403009A ZA200403009A ZA200403009B ZA 200403009 B ZA200403009 B ZA 200403009B ZA 200403009 A ZA200403009 A ZA 200403009A ZA 200403009 A ZA200403009 A ZA 200403009A ZA 200403009 B ZA200403009 B ZA 200403009B

Authority

ZA

South Africa

Prior art keywords

triazine

methyl

triamine

cycloheptyl

ethyl

Prior art date

2001-09-21

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 172
• 150000003918 triazines Chemical class 0.000 title claims description 16
• 150000001875 compounds Chemical class 0.000 claims description 429
• -1 4- methyl-1-piperazinyl Chemical group 0.000 claims description 245
• 230000000694 effects Effects 0.000 claims description 212
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 172
• 125000004432 carbon atom Chemical group C* 0.000 claims description 133
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 89
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• 201000010099 disease Diseases 0.000 claims description 75
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• 125000000217 alkyl group Chemical group 0.000 claims description 73
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• 238000011282 treatment Methods 0.000 claims description 64
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 56
• 229910052736 halogen Inorganic materials 0.000 claims description 55
• 230000004054 inflammatory process Effects 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
• 239000000126 substance Substances 0.000 claims description 49
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• 150000002367 halogens Chemical class 0.000 claims description 48
• 241001465754 Metazoa Species 0.000 claims description 47
• 238000002493 microarray Methods 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 46
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
• 238000003556 assay Methods 0.000 claims description 42
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 38
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
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• 102000005744 Glycoside Hydrolases Human genes 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 102000004190 Enzymes Human genes 0.000 claims description 33
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• 150000001993 dienes Chemical class 0.000 claims description 32
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• 229920006395 saturated elastomer Polymers 0.000 claims description 31
• 150000005671 trienes Chemical class 0.000 claims description 31
• 102000004127 Cytokines Human genes 0.000 claims description 28
• 108090000695 Cytokines Proteins 0.000 claims description 28
• 210000000981 epithelium Anatomy 0.000 claims description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
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• 229910052744 lithium Inorganic materials 0.000 claims description 25
• 229910052749 magnesium Inorganic materials 0.000 claims description 25
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• 229910052708 sodium Inorganic materials 0.000 claims description 25
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• 229910052700 potassium Inorganic materials 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 23
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• 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
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• 125000000304 alkynyl group Chemical group 0.000 claims description 17
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• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 16
• 125000004104 aryloxy group Chemical group 0.000 claims description 16
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• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
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• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
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• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
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• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
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• 210000001644 umbilical artery Anatomy 0.000 claims description 8
• OVMYHFZGNYCTBZ-UHFFFAOYSA-N 2-n-cycloheptyl-4-n-(3-fluoro-4-methoxyphenyl)-6-morpholin-4-yl-1,3,5-triazine-2,4-diamine Chemical compound C1=C(F)C(OC)=CC=C1NC1=NC(NC2CCCCCC2)=NC(N2CCOCC2)=N1 OVMYHFZGNYCTBZ-UHFFFAOYSA-N 0.000 claims description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
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• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 230000002439 hemostatic effect Effects 0.000 claims description 7
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
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• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 5
• 230000030833 cell death Effects 0.000 claims description 5
• 210000003584 mesangial cell Anatomy 0.000 claims description 5
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• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• PISTWJPAJMTDAM-UHFFFAOYSA-N 2-(3-chloro-4-methoxyanilino)-6-(cycloheptylamino)-1h-1,3,5-triazin-4-one Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(O)=NC(NC2CCCCCC2)=N1 PISTWJPAJMTDAM-UHFFFAOYSA-N 0.000 claims description 4
• GBEFQYLIEZKNRQ-UHFFFAOYSA-N 2-n-benzyl-4-n-cycloheptyl-6-n-(4-methoxyphenyl)-2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(NC2CCCCCC2)=NC(N(C)CC=2C=CC=CC=2)=N1 GBEFQYLIEZKNRQ-UHFFFAOYSA-N 0.000 claims description 4
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• FWRLOIVPTIVFDU-UHFFFAOYSA-N 2-[[4-chloro-6-(3-chloro-4-methoxyanilino)-1,3,5-triazin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(Cl)=NC(NC(CO)CO)=N1 FWRLOIVPTIVFDU-UHFFFAOYSA-N 0.000 claims description 3
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• GJBZAECBTWPOEU-UHFFFAOYSA-N 4-n-cycloheptyl-6-n-(3-fluoro-4-methoxyphenyl)-2-n-methyl-2-n-(1-methylpiperidin-4-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound C1=C(F)C(OC)=CC=C1NC1=NC(NC2CCCCCC2)=NC(N(C)C2CCN(C)CC2)=N1 GJBZAECBTWPOEU-UHFFFAOYSA-N 0.000 claims description 3
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• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
• OFAPSLLQSSHRSQ-UHFFFAOYSA-N 1H-triazine-2,4-diamine Chemical compound NN1NC=CC(N)=N1 OFAPSLLQSSHRSQ-UHFFFAOYSA-N 0.000 claims description 2
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• GYYHHHXRLHMHKV-UHFFFAOYSA-N 6-(cyclohexylmethoxy)-2-n,4-n-bis(3-fluoro-4-methoxyphenyl)-1,3,5-triazine-2,4-diamine Chemical compound C1=C(F)C(OC)=CC=C1NC1=NC(NC=2C=C(F)C(OC)=CC=2)=NC(OCC2CCCCC2)=N1 GYYHHHXRLHMHKV-UHFFFAOYSA-N 0.000 claims description 2
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