ZA200600636B - Piperazine derivatives for the treatment of HIV infections - Google Patents

Info

Publication number

ZA200600636B

ZA200600636B ZA200600636A ZA200600636A ZA200600636B ZA 200600636 B ZA200600636 B ZA 200600636B ZA 200600636 A ZA200600636 A ZA 200600636A ZA 200600636 A ZA200600636 A ZA 200600636A ZA 200600636 B ZA200600636 B ZA 200600636B

Authority

ZA

South Africa

Prior art keywords

compound

methyl

formula

phenyl

alkyl

Prior art date

2003-08-14

Links

• Espacenet
• Global Dossier
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• 238000011282 treatment Methods 0.000 title claims description 23
• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 4
• 208000031886 HIV Infections Diseases 0.000 title description 3
• 150000004885 piperazines Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 162
• 150000003839 salts Chemical class 0.000 claims description 52
• 239000000203 mixture Substances 0.000 claims description 48
• 239000012453 solvate Substances 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• -1 thiadiazolyi Chemical group 0.000 claims description 25
• 125000002947 alkylene group Chemical group 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 229940124597 therapeutic agent Drugs 0.000 claims description 12
• 208000030507 AIDS Diseases 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 206010038997 Retroviral infections Diseases 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 5
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• OQRSXFNMNAQFEB-SJORKVTESA-N 4-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 OQRSXFNMNAQFEB-SJORKVTESA-N 0.000 claims description 2
• KVDRFBPETGPOMO-CVEARBPZSA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-4-methoxy-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC)=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 KVDRFBPETGPOMO-CVEARBPZSA-N 0.000 claims description 2
• VMJUDEOSVIYEMQ-SJORKVTESA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-n-cyclopropyl-4-methoxypyridine-2-carboxamide Chemical compound O=C([C@H](C)OC1=CN=C(C=C1OC)C(=O)NC1CC1)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 VMJUDEOSVIYEMQ-SJORKVTESA-N 0.000 claims description 2
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• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
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• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
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• 229920006395 saturated elastomer Polymers 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
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• AHSGKFLIDGDUAT-CABCVRRESA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-4-methoxypyridine-2-carboxamide Chemical compound COC1=CC(C(N)=O)=NC=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 AHSGKFLIDGDUAT-CABCVRRESA-N 0.000 claims 1
• MASAQSXMNRMCGV-SJORKVTESA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-n-ethyl-4-methoxypyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC(OC)=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 MASAQSXMNRMCGV-SJORKVTESA-N 0.000 claims 1
• 238000009472 formulation Methods 0.000 description 29
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• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 17
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