HRP20000621A2 - 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 PDFInfo
- Publication number
- HRP20000621A2 HRP20000621A2 HR20000621A HRP20000621A HRP20000621A2 HR P20000621 A2 HRP20000621 A2 HR P20000621A2 HR 20000621 A HR20000621 A HR 20000621A HR P20000621 A HRP20000621 A HR P20000621A HR P20000621 A2 HRP20000621 A2 HR P20000621A2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- phenoxy
- anilino
- methyl
- benzonitrile
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 12
- 208000031886 HIV Infections Diseases 0.000 title description 5
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 title 1
- -1 cyano, amino, imino, aminocarbonyl Chemical group 0.000 claims description 145
- 150000001875 compounds Chemical class 0.000 claims description 121
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 230000000798 anti-retroviral effect Effects 0.000 claims description 12
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
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- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
- UXIAXNIFQFODAB-UHFFFAOYSA-N 4-[[4-[(5-acetyl-7-methyl-2,3-dihydro-1h-inden-4-yl)oxy]-6-amino-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC(=O)C1=CC(C)=C2CCCC2=C1OC(N=1)=NC(N)=NC=1NC1=CC=C(C#N)C=C1 UXIAXNIFQFODAB-UHFFFAOYSA-N 0.000 claims description 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
- 230000036436 anti-hiv Effects 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AEKHNNJSMVVESS-UHFFFAOYSA-N o-trimethylsilylhydroxylamine Chemical compound C[Si](C)(C)ON AEKHNNJSMVVESS-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
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- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
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- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
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- 235000015320 potassium carbonate Nutrition 0.000 description 1
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- 238000011321 prophylaxis Methods 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
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Classifications
-
- 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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US7963398P | 1998-03-27 | 1998-03-27 | |
EP98201589A EP0945447A1 (en) | 1998-03-27 | 1998-05-14 | Trisubstituted 1,3,5-triazine derivatives for treatment of HIV infections |
PCT/EP1999/002044 WO1999050256A1 (en) | 1998-03-27 | 1999-03-24 | Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections |
Publications (1)
Publication Number | Publication Date |
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HRP20000621A2 true HRP20000621A2 (en) | 2001-04-30 |
Family
ID=22151790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000621A HRP20000621A2 (en) | 1998-03-27 | 2000-09-19 | Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections |
Country Status (33)
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US (3) | US6150360A (es) |
EP (2) | EP0945447A1 (es) |
JP (1) | JP2002511390A (es) |
KR (1) | KR100593396B1 (es) |
CN (1) | CN1157386C (es) |
AP (1) | AP1475A (es) |
AR (1) | AR018169A1 (es) |
AT (1) | ATE295355T1 (es) |
AU (1) | AU758624C (es) |
BG (1) | BG64903B1 (es) |
BR (1) | BR9909197A (es) |
CA (1) | CA2324921C (es) |
DE (1) | DE69925256T2 (es) |
DK (1) | DK1066269T3 (es) |
EA (1) | EA004540B1 (es) |
EE (1) | EE200000535A (es) |
ES (1) | ES2243056T3 (es) |
HK (1) | HK1032394A1 (es) |
HR (1) | HRP20000621A2 (es) |
HU (1) | HUP0101372A3 (es) |
ID (1) | ID26043A (es) |
IL (1) | IL138670A (es) |
NO (1) | NO317425B1 (es) |
NZ (1) | NZ506787A (es) |
OA (1) | OA11493A (es) |
PL (1) | PL194660B1 (es) |
PT (1) | PT1066269E (es) |
SI (1) | SI1066269T1 (es) |
SK (1) | SK14052000A3 (es) |
TR (1) | TR200002761T2 (es) |
TW (1) | TW570917B (es) |
WO (1) | WO1999050256A1 (es) |
ZA (1) | ZA200006042B (es) |
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DE19945982A1 (de) * | 1999-09-24 | 2001-03-29 | Knoll Ag | Geschwindigkeitsbestimmte Partikel |
SK285240B6 (sk) * | 1999-09-24 | 2006-09-07 | Janssen Pharmaceutica N. V. | Antivírusové prostriedky |
US6645964B1 (en) * | 1999-11-29 | 2003-11-11 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agent |
US6906067B2 (en) * | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
US6943161B2 (en) * | 1999-12-28 | 2005-09-13 | Pharmacopela Drug Discovery, Inc. | Pyrimidine and triazine kinase inhibitors |
US20020065270A1 (en) * | 1999-12-28 | 2002-05-30 | Moriarty Kevin Joseph | N-heterocyclic inhibitors of TNF-alpha expression |
EP1282606B1 (en) | 2000-05-08 | 2015-04-22 | Janssen Pharmaceutica NV | Hiv replication inhibiting pyrimidines and triazines |
DK1282607T3 (en) | 2000-05-08 | 2016-02-01 | Janssen Pharmaceutica Nv | Prodrugs of HIV replication inhibiting pyrimidines |
US6858608B2 (en) * | 2001-01-09 | 2005-02-22 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agents |
US6887873B2 (en) * | 2001-03-23 | 2005-05-03 | Aventis Pharma S.A. | Triazine derivatives and their application as antitelomerase agents |
US6958211B2 (en) | 2001-08-08 | 2005-10-25 | Tibotech Bvba | Methods of assessing HIV integrase inhibitor therapy |
JO3429B1 (ar) * | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
KR20040088457A (ko) * | 2001-09-21 | 2004-10-16 | 레디 유에스 테라퓨틱스 인코포레이티드 | 신규 트리아진 화합물 제조방법 및 조성물 |
US7163943B2 (en) | 2001-09-21 | 2007-01-16 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7173032B2 (en) * | 2001-09-21 | 2007-02-06 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7132423B2 (en) * | 2001-09-21 | 2006-11-07 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7169785B2 (en) * | 2001-09-21 | 2007-01-30 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7112587B2 (en) * | 2001-09-21 | 2006-09-26 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
WO2003032903A2 (en) * | 2001-10-12 | 2003-04-24 | New York University | Trisubstituted triazines compounds with antitubulin activity |
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AR039540A1 (es) * | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
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WO2004074266A1 (en) * | 2003-02-07 | 2004-09-02 | Janssen Pharmaceutica N.V. | Hiv inhibiting 1,2,4-triazines |
US20070232572A1 (en) * | 2003-02-07 | 2007-10-04 | Aventis Pharma S.A. | Chemical derivatives as antitelomerase agents which bind specifically to the G-quadruplex DNA structures and their application as a specific anticancer agent |
CL2004000303A1 (es) * | 2003-02-20 | 2005-04-08 | Tibotec Pharm Ltd | Compuestos derivados de pirimidinas y triazinas; proceso de preparacion; composicion farmaceutica; y su uso para inhibir la replicacion del vih. |
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CA2577588C (en) | 2004-10-29 | 2013-09-10 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting bicyclic pyrimidine derivatives |
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CN101245051B (zh) * | 2005-12-22 | 2011-04-20 | 中国科学院上海药物研究所 | 2,4-二取代氨基-6-取代-[1,3,5]三嗪类化合物、其制备方法、药物组合物及用途 |
EP2004632B1 (en) | 2006-03-30 | 2014-03-12 | Janssen R&D Ireland | Hiv inhibiting 5-amido substituted pyrimidines |
AU2007341228B2 (en) | 2006-12-29 | 2013-04-18 | Janssen Sciences Ireland Uc | HIV inhibiting 5,6-substituted pyrimidines |
BRPI0720858B8 (pt) | 2006-12-29 | 2021-05-25 | Janssen R & D Ireland | pirimidinas 6-substituídas inibidoras de hiv e composição farmacêutica que as compreende |
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GB201204756D0 (en) | 2012-03-19 | 2012-05-02 | Lewi Paulus J | Triazines with suitable spacers for treatment and/or prevention of HIV infections |
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US9914709B2 (en) * | 2013-06-21 | 2018-03-13 | Yale University | Compositions and methods of treating HIV-1 infections using same |
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US11839616B2 (en) | 2017-08-24 | 2023-12-12 | The Regents Of The University Of California | Ocular pharmaceutical compositions |
CN109053613A (zh) * | 2018-07-04 | 2018-12-21 | 复旦大学 | 含有联苯结构的二芳基三嗪类化合物及其制备方法和用途 |
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WO1999036410A1 (en) * | 1998-01-13 | 1999-07-22 | Scriptgen Pharmaceuticals, Inc. | Triazine antiviral compounds |
-
1998
- 1998-05-14 EP EP98201589A patent/EP0945447A1/en not_active Withdrawn
-
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