NO317425B1 - Trisubstituerte 1,3,5-triazinderivater for behandling av HIV-infeksjoner - Google Patents
Trisubstituerte 1,3,5-triazinderivater for behandling av HIV-infeksjoner Download PDFInfo
- Publication number
- NO317425B1 NO317425B1 NO20004809A NO20004809A NO317425B1 NO 317425 B1 NO317425 B1 NO 317425B1 NO 20004809 A NO20004809 A NO 20004809A NO 20004809 A NO20004809 A NO 20004809A NO 317425 B1 NO317425 B1 NO 317425B1
- Authority
- NO
- Norway
- Prior art keywords
- amine
- benzonitrile
- amino
- triazin
- formula
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 17
- 208000031886 HIV Infections Diseases 0.000 title description 6
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 title 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 140
- 150000001875 compounds Chemical class 0.000 claims description 118
- -1 C1-6alkyloxy Chemical group 0.000 claims description 65
- 150000001412 amines Chemical class 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 12
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 claims description 11
- 230000000798 anti-retroviral effect Effects 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
- ATDIROHVRVQMRO-UHFFFAOYSA-N 2,6-dibromo-4-methylaniline Chemical compound CC1=CC(Br)=C(N)C(Br)=C1 ATDIROHVRVQMRO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- FNSAKXLEFPFZOM-UHFFFAOYSA-N 2,4,6-trimethoxyaniline Chemical compound COC1=CC(OC)=C(N)C(OC)=C1 FNSAKXLEFPFZOM-UHFFFAOYSA-N 0.000 claims description 4
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 claims description 4
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 4
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 4
- 230000036436 anti-hiv Effects 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- QISTWSMZJRTDCS-UHFFFAOYSA-N (2,4-dichloro-6-methylphenyl)methanamine Chemical compound CC1=CC(Cl)=CC(Cl)=C1CN QISTWSMZJRTDCS-UHFFFAOYSA-N 0.000 claims description 2
- QOWBXWFYRXSBAS-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(OC)=C1 QOWBXWFYRXSBAS-UHFFFAOYSA-N 0.000 claims description 2
- BDSDVMMCXGKRJO-UHFFFAOYSA-N 1-(2-amino-4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1N BDSDVMMCXGKRJO-UHFFFAOYSA-N 0.000 claims description 2
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 claims description 2
- NATVSFWWYVJTAZ-UHFFFAOYSA-N 2,4,6-trichloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1Cl NATVSFWWYVJTAZ-UHFFFAOYSA-N 0.000 claims description 2
- OCJPQZFOBGQYEA-UHFFFAOYSA-N 2,4-dichloro-6-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(F)(F)F OCJPQZFOBGQYEA-UHFFFAOYSA-N 0.000 claims description 2
- UAISVUGQLKXPFF-UHFFFAOYSA-N 2,4-dichloro-6-methylaniline Chemical compound CC1=CC(Cl)=CC(Cl)=C1N UAISVUGQLKXPFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- CJEBZUFROMNDEK-UHFFFAOYSA-N 2,6-dibromo-4-propan-2-ylaniline Chemical compound CC(C)C1=CC(Br)=C(N)C(Br)=C1 CJEBZUFROMNDEK-UHFFFAOYSA-N 0.000 claims description 2
- ITNMAZSPBLRJLU-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C(C(F)(F)F)C=C1Cl ITNMAZSPBLRJLU-UHFFFAOYSA-N 0.000 claims description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 claims description 2
- WUJKFVGKLTWVSQ-UHFFFAOYSA-N 2-bromo-4,6-difluoroaniline Chemical compound NC1=C(F)C=C(F)C=C1Br WUJKFVGKLTWVSQ-UHFFFAOYSA-N 0.000 claims description 2
- LKAQFOKMMXWRRQ-UHFFFAOYSA-N 2-chloro-4,6-dimethylaniline Chemical compound CC1=CC(C)=C(N)C(Cl)=C1 LKAQFOKMMXWRRQ-UHFFFAOYSA-N 0.000 claims description 2
- OXINUINVVAJJSE-UHFFFAOYSA-N 2-chloro-4-fluoro-5-methylaniline Chemical compound CC1=CC(N)=C(Cl)C=C1F OXINUINVVAJJSE-UHFFFAOYSA-N 0.000 claims description 2
- DDTKYVBFPULMGN-UHFFFAOYSA-N 2-methyl-6-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(C)=C1N DDTKYVBFPULMGN-UHFFFAOYSA-N 0.000 claims description 2
- MVLMPTBHZPYDBZ-UHFFFAOYSA-N 3-bromo-2,4,6-trimethylaniline Chemical compound CC1=CC(C)=C(Br)C(C)=C1N MVLMPTBHZPYDBZ-UHFFFAOYSA-N 0.000 claims description 2
- FGMXFOTYCHZCLA-UHFFFAOYSA-N 3-chloro-2,6-dimethylaniline Chemical compound CC1=CC=C(Cl)C(C)=C1N FGMXFOTYCHZCLA-UHFFFAOYSA-N 0.000 claims description 2
- NAHFVGNZSYSRML-UHFFFAOYSA-N 4-[[4-(4-acetyl-2,6-dimethylphenoxy)-6-amino-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C(=O)C)=CC(C)=C1OC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 NAHFVGNZSYSRML-UHFFFAOYSA-N 0.000 claims description 2
- ACFLKRQYMVDGHR-UHFFFAOYSA-N 4-[[4-amino-6-(2,4,6-tribromophenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound N=1C(OC=2C(=CC(Br)=CC=2Br)Br)=NC(N)=NC=1NC1=CC=C(C#N)C=C1 ACFLKRQYMVDGHR-UHFFFAOYSA-N 0.000 claims description 2
- CDMKXIMAQHVWRQ-UHFFFAOYSA-N 4-[[4-amino-6-(2,4,6-trimethylphenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1OC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 CDMKXIMAQHVWRQ-UHFFFAOYSA-N 0.000 claims description 2
- RQDRINOZMJPFLY-UHFFFAOYSA-N 4-[[4-amino-6-(2,6-dibromo-4-methylphenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound BrC1=CC(C)=CC(Br)=C1OC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 RQDRINOZMJPFLY-UHFFFAOYSA-N 0.000 claims description 2
- UFXAUTDOHDOICK-UHFFFAOYSA-N 4-[[4-amino-6-(2,6-dimethyl-4-nitrophenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1OC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 UFXAUTDOHDOICK-UHFFFAOYSA-N 0.000 claims description 2
- SEFNHVPFQAGLEC-UHFFFAOYSA-N 4-[[4-amino-6-(4-formyl-2,6-dimethylphenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C=O)=CC(C)=C1OC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 SEFNHVPFQAGLEC-UHFFFAOYSA-N 0.000 claims description 2
- BEJYDMQQZUACPW-UHFFFAOYSA-N 4-bromo-2,6-diethylaniline Chemical compound CCC1=CC(Br)=CC(CC)=C1N BEJYDMQQZUACPW-UHFFFAOYSA-N 0.000 claims description 2
- QGLAYJCJLHNIGJ-UHFFFAOYSA-N 4-bromo-2,6-dimethylaniline Chemical compound CC1=CC(Br)=CC(C)=C1N QGLAYJCJLHNIGJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- UPVUQELOASQBMY-UHFFFAOYSA-N methyl 2-amino-3,4,5-trimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C(OC)=C1N UPVUQELOASQBMY-UHFFFAOYSA-N 0.000 claims description 2
- HKABSXHXKCTVGW-UHFFFAOYSA-N n,2,4,6-tetramethylaniline Chemical compound CNC1=C(C)C=C(C)C=C1C HKABSXHXKCTVGW-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 7
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- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229940054565 sustiva Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
- 229960004517 thymopentin Drugs 0.000 description 1
- DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 description 1
- YFNGWGVTFYSJHE-UHFFFAOYSA-K trisodium;phosphonoformate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O YFNGWGVTFYSJHE-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| NO20004809D0 NO20004809D0 (no) | 2000-09-26 |
| NO20004809L NO20004809L (no) | 2000-11-24 |
| NO317425B1 true NO317425B1 (no) | 2004-10-25 |
Family
ID=22151790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20004809A NO317425B1 (no) | 1998-03-27 | 2000-09-26 | Trisubstituerte 1,3,5-triazinderivater for behandling av HIV-infeksjoner |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US6150360A (bg) |
| EP (2) | EP0945447A1 (bg) |
| JP (1) | JP2002511390A (bg) |
| KR (1) | KR100593396B1 (bg) |
| CN (1) | CN1157386C (bg) |
| AP (1) | AP1475A (bg) |
| AR (1) | AR018169A1 (bg) |
| AT (1) | ATE295355T1 (bg) |
| AU (1) | AU758624C (bg) |
| BG (1) | BG64903B1 (bg) |
| BR (1) | BR9909197A (bg) |
| CA (1) | CA2324921C (bg) |
| DE (1) | DE69925256T2 (bg) |
| DK (1) | DK1066269T3 (bg) |
| EA (1) | EA004540B1 (bg) |
| EE (1) | EE200000535A (bg) |
| ES (1) | ES2243056T3 (bg) |
| HK (1) | HK1032394A1 (bg) |
| HR (1) | HRP20000621A2 (bg) |
| HU (1) | HUP0101372A3 (bg) |
| ID (1) | ID26043A (bg) |
| IL (1) | IL138670A (bg) |
| NO (1) | NO317425B1 (bg) |
| NZ (1) | NZ506787A (bg) |
| OA (1) | OA11493A (bg) |
| PL (1) | PL194660B1 (bg) |
| PT (1) | PT1066269E (bg) |
| SI (1) | SI1066269T1 (bg) |
| SK (1) | SK14052000A3 (bg) |
| TR (1) | TR200002761T2 (bg) |
| TW (1) | TW570917B (bg) |
| WO (1) | WO1999050256A1 (bg) |
| ZA (1) | ZA200006042B (bg) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19945982A1 (de) * | 1999-09-24 | 2001-03-29 | Knoll Ag | Geschwindigkeitsbestimmte Partikel |
| JP4919566B2 (ja) * | 1999-09-24 | 2012-04-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗ウイルス組成物 |
| US6645964B1 (en) * | 1999-11-29 | 2003-11-11 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agent |
| US6943161B2 (en) * | 1999-12-28 | 2005-09-13 | Pharmacopela Drug Discovery, Inc. | Pyrimidine and triazine kinase inhibitors |
| US6906067B2 (en) * | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
| US20020065270A1 (en) * | 1999-12-28 | 2002-05-30 | Moriarty Kevin Joseph | N-heterocyclic inhibitors of TNF-alpha expression |
| AU783981C (en) | 2000-05-08 | 2007-05-03 | Janssen Pharmaceutica N.V. | HIV replication inhibitors |
| EP1282607B1 (en) | 2000-05-08 | 2015-11-11 | 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 |
| US7163943B2 (en) * | 2001-09-21 | 2007-01-16 | 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 |
| PL369600A1 (en) * | 2001-09-21 | 2005-05-02 | 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 |
| US7132423B2 (en) * | 2001-09-21 | 2006-11-07 | 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 |
| WO2003032903A2 (en) * | 2001-10-12 | 2003-04-24 | New York University | Trisubstituted triazines compounds with antitubulin activity |
| WO2003037346A1 (en) * | 2001-10-31 | 2003-05-08 | Cell Therapeutics, Inc. | 6-phenyl-n-phenyl-(1,3,5) -triazine-2,4-diamine derivatives and related compounds with lysophphosphatidic acid acyltransferase beta (lpaat-beta) inhibitory activity for use in the treatment of cancer |
| CN102151273B (zh) * | 2002-02-05 | 2015-11-25 | 安斯泰来制药有限公司 | 2,4,6-三氨基-1,3,5-三嗪衍生物 |
| AR039540A1 (es) * | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
| US7419984B2 (en) * | 2002-10-17 | 2008-09-02 | Cell Therapeutics, Inc. | Pyrimidines and uses thereof |
| 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 |
| CL2004000306A1 (es) * | 2003-02-20 | 2005-04-08 | Tibotec Pharm Ltd | Compuestos derivados de pirimidina sustituidas con indano; proceso para su preparacion; composicion farmaceutica que lo comprende; combinacion farmaceutica; y su uso para el tratamiento o profilaxis de una enfermedad infecciosa. |
| US6875781B2 (en) * | 2003-04-04 | 2005-04-05 | Cell Therapeutics, Inc. | Pyridines and uses thereof |
| US20060172010A1 (en) | 2003-07-17 | 2006-08-03 | Gael Lamoureux | Process for preparing particles containing an antiviral |
| JP2006528640A (ja) * | 2003-07-22 | 2006-12-21 | ニューロジェン・コーポレーション | 置換ピリジン−２−イルアミン類縁体 |
| US7335770B2 (en) * | 2004-03-24 | 2008-02-26 | Reddy U5 Therapeutics, Inc. | Triazine compounds and their analogs, compositions, and methods |
| CN101035773B (zh) | 2004-08-10 | 2012-06-06 | 詹森药业有限公司 | 抑制hiv的1,2,4-三嗪-6-酮衍生物 |
| TW200626560A (en) | 2004-09-30 | 2006-08-01 | Tibotec Pharm Ltd | HIV inhibiting 5-carbo-or heterocyclic substituted pyrimidines |
| TW200626561A (en) | 2004-09-30 | 2006-08-01 | Tibotec Pharm Ltd | HIV inhibiting 5-substituted pyrimidines |
| TW200626574A (en) | 2004-09-30 | 2006-08-01 | Tibotec Pharm Ltd | HIV inhibiting 5-heterocyclyl pyrimidines |
| RU2403254C2 (ru) | 2004-10-29 | 2010-11-10 | Тиботек Фармасьютикалз Лтд. | Бициклические производные пиримидина, ингибирующие вич |
| US7592451B2 (en) * | 2005-06-23 | 2009-09-22 | New York University | Treatment for diabetes and obesity as well as method of screening compounds useful for such treatments |
| 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 |
| CN101573343B (zh) | 2006-12-29 | 2016-02-24 | 爱尔兰詹森科学公司 | 抑制人免疫缺陷病毒的6-取代的嘧啶 |
| CA2923637C (en) | 2006-12-29 | 2018-10-02 | Janssen Sciences Ireland Uc | Hiv inhibiting 5,6-substituted pyrimidines |
| CN103476769B (zh) | 2010-10-27 | 2016-06-01 | 沃尔特及伊莱萨霍尔医学研究院 | 抗癌剂 |
| GB201119358D0 (en) | 2011-11-10 | 2011-12-21 | Lewi Paulus J | Disubstituted triazine dimers for treatment and/or prevention of infectious diseases |
| GB201204756D0 (en) | 2012-03-19 | 2012-05-02 | Lewi Paulus J | Triazines with suitable spacers for treatment and/or prevention of HIV infections |
| WO2014072419A1 (en) | 2012-11-08 | 2014-05-15 | Universiteit Antwerpen | Novel anti-hiv compounds |
| US9914709B2 (en) * | 2013-06-21 | 2018-03-13 | Yale University | Compositions and methods of treating HIV-1 infections using same |
| EP3122736A1 (en) * | 2014-03-28 | 2017-02-01 | Basf Se | Diaminotriazine derivatives as herbicides |
| US10604492B2 (en) | 2015-12-24 | 2020-03-31 | The Regents Of The Universtiy Of California | CFTR regulators and methods of use thereof |
| CN111629730A (zh) | 2017-08-24 | 2020-09-04 | 加利福尼亚大学董事会 | 眼部药物组合物 |
| 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2742466A (en) * | 1956-04-17 | Chx n nhx c c | ||
| US2671810A (en) * | 1952-05-24 | 1954-03-09 | Du Pont | Long-chain diketones |
| BE754242A (fr) * | 1970-07-15 | 1971-02-01 | Geigy Ag J R | Diamino-s-triazines et dinitro-s-triazines |
| US4096206A (en) | 1976-02-09 | 1978-06-20 | Borg-Warner Corporation | Flame-retardant triazines |
| US4652645A (en) | 1983-11-16 | 1987-03-24 | Ciba-Geigy Corporation | Cationic compounds |
| EP0541966A3 (en) * | 1991-11-15 | 1994-09-07 | American Cyanamid Co | Process for preparing amide derivatives from halomines and acid halides |
| US5283274A (en) * | 1992-06-19 | 1994-02-01 | Uniroyal Chemical Company, Inc. | Substituted pyrimidines and substituted triazines as rubber-to-metal adhesion promoters |
| EP0723533A1 (en) | 1993-10-12 | 1996-07-31 | The Du Pont Merck Pharmaceutical Company | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof |
| GB9519197D0 (en) * | 1995-09-20 | 1995-11-22 | Affinity Chromatography Ltd | Novel affinity ligands and their use |
| CN1163401A (zh) * | 1996-02-13 | 1997-10-29 | 李占元 | 全自动血球计数仪试剂及配制方法 |
| CA2318362A1 (en) * | 1998-01-13 | 1999-07-22 | Sharon T. Cload | Triazine antiviral compounds |
-
1998
- 1998-05-14 EP EP98201589A patent/EP0945447A1/en not_active Withdrawn
-
1999
- 1999-03-24 EE EEP200000535A patent/EE200000535A/xx unknown
- 1999-03-24 PL PL99343195A patent/PL194660B1/pl not_active IP Right Cessation
- 1999-03-24 HU HU0101372A patent/HUP0101372A3/hu unknown
- 1999-03-24 DK DK99917863T patent/DK1066269T3/da active
- 1999-03-24 KR KR1020007007971A patent/KR100593396B1/ko not_active IP Right Cessation
- 1999-03-24 PT PT99917863T patent/PT1066269E/pt unknown
- 1999-03-24 CN CNB998044474A patent/CN1157386C/zh not_active Expired - Fee Related
- 1999-03-24 TR TR2000/02761T patent/TR200002761T2/xx unknown
- 1999-03-24 AP APAP/P/2000/001913A patent/AP1475A/en active
- 1999-03-24 EP EP99917863A patent/EP1066269B1/en not_active Expired - Lifetime
- 1999-03-24 AU AU35997/99A patent/AU758624C/en not_active Ceased
- 1999-03-24 SK SK1405-2000A patent/SK14052000A3/sk unknown
- 1999-03-24 ES ES99917863T patent/ES2243056T3/es not_active Expired - Lifetime
- 1999-03-24 JP JP2000541160A patent/JP2002511390A/ja active Pending
- 1999-03-24 NZ NZ506787A patent/NZ506787A/xx unknown
- 1999-03-24 WO PCT/EP1999/002044 patent/WO1999050256A1/en not_active Application Discontinuation
- 1999-03-24 AT AT99917863T patent/ATE295355T1/de not_active IP Right Cessation
- 1999-03-24 DE DE69925256T patent/DE69925256T2/de not_active Expired - Fee Related
- 1999-03-24 BR BR9909197-6A patent/BR9909197A/pt not_active Application Discontinuation
- 1999-03-24 CA CA002324921A patent/CA2324921C/en not_active Expired - Fee Related
- 1999-03-24 SI SI9930807T patent/SI1066269T1/xx unknown
- 1999-03-24 EA EA200000993A patent/EA004540B1/ru not_active IP Right Cessation
- 1999-03-24 ID IDW20001895A patent/ID26043A/id unknown
- 1999-03-25 US US09/276,362 patent/US6150360A/en not_active Expired - Fee Related
- 1999-03-26 AR ARP990101363A patent/AR018169A1/es unknown
- 1999-03-26 TW TW088104756A patent/TW570917B/zh not_active IP Right Cessation
-
2000
- 2000-08-08 US US09/634,340 patent/US6372729B1/en not_active Expired - Fee Related
- 2000-08-28 BG BG104716A patent/BG64903B1/bg unknown
- 2000-09-19 HR HR20000621A patent/HRP20000621A2/hr not_active Application Discontinuation
- 2000-09-25 IL IL13867000A patent/IL138670A/xx not_active IP Right Cessation
- 2000-09-26 NO NO20004809A patent/NO317425B1/no unknown
- 2000-09-27 OA OA1200000266A patent/OA11493A/en unknown
- 2000-10-26 ZA ZA200006042A patent/ZA200006042B/xx unknown
-
2001
- 2001-04-20 HK HK01102801A patent/HK1032394A1/xx not_active IP Right Cessation
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2002
- 2002-02-05 US US10/067,383 patent/US6774235B2/en not_active Expired - Fee Related
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