ZA200408905B - Using a selective iNOS inhibitor for the treatment of respiratory diseases and conditions - Google Patents

Info

Publication number

ZA200408905B

ZA200408905B ZA200408905A ZA200408905A ZA200408905B ZA 200408905 B ZA200408905 B ZA 200408905B ZA 200408905 A ZA200408905 A ZA 200408905A ZA 200408905 A ZA200408905 A ZA 200408905A ZA 200408905 B ZA200408905 B ZA 200408905B

Authority

ZA

South Africa

Prior art keywords

alkyl

optionally substituted

group

amino

halo

Prior art date

2002-05-16

Links

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• Global Dossier
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• 238000011282 treatment Methods 0.000 title claims description 57
• 239000003112 inhibitor Substances 0.000 title claims description 39
• 208000023504 respiratory system disease Diseases 0.000 title claims description 27
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• 101710089543 Nitric oxide synthase, inducible Proteins 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 285
• 239000000203 mixture Substances 0.000 claims description 170
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• 125000005843 halogen group Chemical group 0.000 claims description 150
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• 238000000034 method Methods 0.000 claims description 131
• 150000001875 compounds Chemical class 0.000 claims description 108
• 229910052739 hydrogen Inorganic materials 0.000 claims description 107
• 238000006243 chemical reaction Methods 0.000 claims description 105
• 208000006673 asthma Diseases 0.000 claims description 100
• 150000003839 salts Chemical class 0.000 claims description 90
• 239000001257 hydrogen Substances 0.000 claims description 73
• 150000002431 hydrogen Chemical class 0.000 claims description 66
• 229940119568 Inducible nitric oxide synthase inhibitor Drugs 0.000 claims description 64
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 239000000126 substance Substances 0.000 claims description 44
• 230000002265 prevention Effects 0.000 claims description 42
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• 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
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• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 29
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• 125000004429 atom Chemical group 0.000 claims description 18
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• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
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• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 5
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• 241000272201 Columbiformes Species 0.000 claims description 4
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 208000027418 Wounds and injury Diseases 0.000 claims description 4
• 239000002253 acid Substances 0.000 claims description 4
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• 125000002252 acyl group Chemical group 0.000 claims description 4
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• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
• 125000000539 amino acid group Chemical group 0.000 claims description 4
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
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• 201000009267 bronchiectasis Diseases 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 238000007675 cardiac surgery Methods 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
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• FVQYBAASQSUZOP-UHFFFAOYSA-N tert-butyl n-(4-chlorobut-2-ynyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC#CCCl FVQYBAASQSUZOP-UHFFFAOYSA-N 0.000 description 1
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• PVNUIRUAPVSSOK-UHFFFAOYSA-N tert-butylimino(tripyrrolidin-1-yl)-$l^{5}-phosphane Chemical compound C1CCCN1P(N1CCCC1)(=NC(C)(C)C)N1CCCC1 PVNUIRUAPVSSOK-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 230000005945 translocation Effects 0.000 description 1
• GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
• DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
• 230000001960 triggered effect Effects 0.000 description 1
• PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1
• 229940124549 vasodilator Drugs 0.000 description 1
• 239000003071 vasodilator agent Substances 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1