NO311614B1 - Substituerte diamino-1,3,5-triazinderivater - Google Patents
Substituerte diamino-1,3,5-triazinderivater Download PDFInfo
- Publication number
- NO311614B1 NO311614B1 NO19974368A NO974368A NO311614B1 NO 311614 B1 NO311614 B1 NO 311614B1 NO 19974368 A NO19974368 A NO 19974368A NO 974368 A NO974368 A NO 974368A NO 311614 B1 NO311614 B1 NO 311614B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- alkyl
- compound
- independently selected
- amino
- Prior art date
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 151
- 239000000543 intermediate Substances 0.000 claims description 66
- -1 amino, imino, aminocarbonyl Chemical group 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 125000001475 halogen functional group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 239000012442 inert solvent Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000001041 indolyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 230000000798 anti-retroviral effect Effects 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 230000036436 anti-hiv Effects 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- BYARTTHGWGIRGS-UHFFFAOYSA-N 4-[[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound N=1C(NC=2C=CC(=CC=2)C#N)=NC(N)=NC=1CC1=C(Cl)C=CC=C1Cl BYARTTHGWGIRGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
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- 239000002244 precipitate Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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- 239000007787 solid Substances 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
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- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
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- 241001143131 Ononis natrix Species 0.000 description 4
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- 238000003818 flash chromatography Methods 0.000 description 4
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- 239000011780 sodium chloride Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
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- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- 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
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- A61P31/14—Antivirals for RNA viruses
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2726096P | 1996-10-01 | 1996-10-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO974368D0 NO974368D0 (no) | 1997-09-22 |
| NO974368L NO974368L (no) | 1998-04-02 |
| NO311614B1 true NO311614B1 (no) | 2001-12-17 |
Family
ID=21836641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19974368A NO311614B1 (no) | 1996-10-01 | 1997-09-22 | Substituerte diamino-1,3,5-triazinderivater |
Country Status (34)
| Country | Link |
|---|---|
| US (4) | US6380194B1 (id) |
| EP (1) | EP0834507B1 (id) |
| JP (1) | JP4127882B2 (id) |
| KR (1) | KR100478846B1 (id) |
| CN (1) | CN1083438C (id) |
| AP (1) | AP914A (id) |
| AR (1) | AR008864A1 (id) |
| AT (1) | ATE267179T1 (id) |
| AU (1) | AU740809B2 (id) |
| BR (1) | BR9704937A (id) |
| CA (1) | CA2216486A1 (id) |
| CZ (1) | CZ297333B6 (id) |
| DE (1) | DE69729153T2 (id) |
| DK (1) | DK0834507T3 (id) |
| EE (1) | EE03826B1 (id) |
| ES (1) | ES2221679T3 (id) |
| HK (1) | HK1009676A1 (id) |
| HR (1) | HRP970526B1 (id) |
| HU (1) | HU225270B1 (id) |
| ID (1) | ID19599A (id) |
| IL (1) | IL121849A (id) |
| MY (1) | MY123803A (id) |
| NO (1) | NO311614B1 (id) |
| NZ (1) | NZ328854A (id) |
| OA (1) | OA10620A (id) |
| PL (1) | PL190155B1 (id) |
| PT (1) | PT834507E (id) |
| RU (1) | RU2186774C2 (id) |
| SG (1) | SG53075A1 (id) |
| SI (1) | SI0834507T1 (id) |
| SK (1) | SK285241B6 (id) |
| TR (1) | TR199701070A2 (id) |
| TW (1) | TW411335B (id) |
| ZA (1) | ZA978766B (id) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO311614B1 (no) * | 1996-10-01 | 2001-12-17 | Janssen Pharmaceutica Nv | Substituerte diamino-1,3,5-triazinderivater |
| KR100658489B1 (ko) * | 1998-11-10 | 2006-12-18 | 얀센 파마슈티카 엔.브이. | Ｈｉｖ 복제를 억제하는 피리미딘 |
| SI1129079T1 (sl) * | 1998-11-10 | 2006-06-30 | Janssen Pharmaceutica Nv | 2,4-disubstituirani triazinski derivati z anti-HIV aktivnostjo |
| 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 |
| DE19945982A1 (de) * | 1999-09-24 | 2001-03-29 | Knoll Ag | Geschwindigkeitsbestimmte Partikel |
| US6906067B2 (en) | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
| AU2735201A (en) * | 1999-12-28 | 2001-07-09 | Pharmacopeia, Inc. | Pyrimidine and triazine kinase inhibitors |
| EP1282607B1 (en) | 2000-05-08 | 2015-11-11 | Janssen Pharmaceutica NV | Prodrugs of hiv replication inhibiting pyrimidines |
| AU783981C (en) | 2000-05-08 | 2007-05-03 | Janssen Pharmaceutica N.V. | HIV replication inhibitors |
| CA2451125A1 (en) * | 2001-06-26 | 2003-01-09 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of tnf-alpha expression |
| US6958211B2 (en) | 2001-08-08 | 2005-10-25 | Tibotech Bvba | Methods of assessing HIV integrase inhibitor therapy |
| NZ531853A (en) | 2001-11-01 | 2006-02-24 | Janssen Pharmaceutica Nv | Heteroaryl amines as glycogen synthase kinase 3beta inhibitors (gsk3 inhibitors) |
| AU2002363174B2 (en) | 2001-11-01 | 2008-09-25 | Janssen Pharmaceutica N.V. | Amide derivatives as glycogen synthase kinase 3-beta inhibitors |
| EP1509515A4 (en) | 2002-05-16 | 2006-07-05 | Cytovia Inc | SUBSTITUTED 4-ARYL-4H-PYRROLO 2,3-H | CHROMENES AND ANALOGUES AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THEIR USE |
| AU2003241482A1 (en) * | 2002-05-16 | 2003-12-02 | Cytovia, Inc. | Substituted 4h-chromenes, 2h-chromenes, chromans and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| AU2002350719A1 (en) * | 2002-11-29 | 2004-06-23 | Janssen Pharmaceutica N.V. | Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base |
| WO2004074266A1 (en) | 2003-02-07 | 2004-09-02 | Janssen Pharmaceutica N.V. | Hiv inhibiting 1,2,4-triazines |
| 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. |
| WO2005003103A2 (en) * | 2003-06-30 | 2005-01-13 | Astrazeneca Ab | 2, 4, 6-tri-substituted 6-membered heterocycles and their use in the treatment of neurodegenerative diseases |
| 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 |
| WO2006024175A1 (en) * | 2004-09-03 | 2006-03-09 | Prometic Biosciences Inc. | 2,4,6-TRIAMINO-S-TRIAZINE-BASED COMPOUNDS WHICH BIND TO THE TAIL (Fc) PORTION OF IMMUNOGLOBULINS AND THEIR USE |
| TW200626561A (en) | 2004-09-30 | 2006-08-01 | Tibotec Pharm Ltd | HIV inhibiting 5-substituted pyrimidines |
| TW200626560A (en) | 2004-09-30 | 2006-08-01 | Tibotec Pharm Ltd | HIV inhibiting 5-carbo-or heterocyclic 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 |
| EP1890703B1 (en) | 2005-06-14 | 2016-05-11 | Taigen Biotechnology | Pyrimidine compounds as chemokine receptors inhibitors |
| US8193206B2 (en) | 2005-06-14 | 2012-06-05 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
| EP2004632B1 (en) | 2006-03-30 | 2014-03-12 | Janssen R&D Ireland | Hiv inhibiting 5-amido substituted pyrimidines |
| CA2923637C (en) * | 2006-12-29 | 2018-10-02 | Janssen Sciences Ireland Uc | Hiv inhibiting 5,6-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 |
| WO2008131547A1 (en) * | 2007-04-30 | 2008-11-06 | Prometic Biosciences Inc. | 'triazine derivatives, compositions containing such derivatives, and methods of treatment of cancer and autoimmune diseases using such derivatives' |
| US8372849B2 (en) * | 2008-04-21 | 2013-02-12 | Taigen Biotechnology Co., Ltd. | Heterocyclic compounds |
| WO2010056847A2 (en) | 2008-11-13 | 2010-05-20 | Taigen Biotechnology Co., Ltd. | Lyophilization formulation |
| US9058223B2 (en) * | 2011-04-22 | 2015-06-16 | Microsoft Technology Licensing Llc | Parallel entropy encoding on GPU |
| US9549558B2 (en) * | 2012-10-24 | 2017-01-24 | Basf Se | Herbicidal azines |
| CN106458937A (zh) * | 2014-04-11 | 2017-02-22 | 巴斯夫欧洲公司 | 作为除草剂的二氨基三嗪衍生物 |
| WO2016059647A2 (en) * | 2014-10-13 | 2016-04-21 | SHRI CHHATRAPTI SHIVAJI COLLEGE Maharashtra, India) | Triaminotriazine picolinonitrile derivatives as potent reverse transcriptase inhibitor of hiv-1 |
| CN105837525B (zh) * | 2016-03-25 | 2019-05-28 | 浙江工业大学 | 2,4-二胺-1,3,5-三嗪类化合物及其制备方法与应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE226474C (id) | ||||
| US2309663A (en) * | 1943-01-26 | Process fok preparing substituted | ||
| US2817814A (en) | 1953-08-13 | 1957-12-24 | Gen Electric | Corona detection probe |
| GB771327A (en) | 1953-10-26 | 1957-03-27 | Monsanto Chemicals | Production of heat hardenable melamine-formaldehyde condensation products |
| US2817614A (en) * | 1953-10-26 | 1957-12-24 | Monsanto Chemicals | Internally plasticized melamine resins and laminates made therewith |
| JPS4927592B1 (id) * | 1970-05-13 | 1974-07-18 | ||
| GB1390235A (en) | 1971-08-07 | 1975-04-09 | Kakenyaku Kako Kk | 2-amino-4,6substituted-s triazines and methods for their preparation |
| DE3724379A1 (de) * | 1987-07-23 | 1989-02-02 | Bayer Ag | Verfahren zur herstellung feinteiliger magnetischer hexaferritpigmente |
| WO1993010116A1 (en) * | 1991-11-12 | 1993-05-27 | Pfizer Inc. | Triazine derivatives for enhancing antitumor activity |
| US5516775A (en) * | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
| WO1995010506A1 (en) * | 1993-10-12 | 1995-04-20 | The Du Pont Merck Pharmaceutical Company | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof |
| NO311614B1 (no) * | 1996-10-01 | 2001-12-17 | Janssen Pharmaceutica Nv | Substituerte diamino-1,3,5-triazinderivater |
-
1997
- 1997-09-22 NO NO19974368A patent/NO311614B1/no unknown
- 1997-09-23 SG SG1997003520A patent/SG53075A1/en unknown
- 1997-09-23 CZ CZ0299397A patent/CZ297333B6/cs not_active IP Right Cessation
- 1997-09-24 DE DE69729153T patent/DE69729153T2/de not_active Expired - Fee Related
- 1997-09-24 DK DK97202917T patent/DK0834507T3/da active
- 1997-09-24 SI SI9730663T patent/SI0834507T1/xx unknown
- 1997-09-24 PT PT97202917T patent/PT834507E/pt unknown
- 1997-09-24 EP EP97202917A patent/EP0834507B1/en not_active Expired - Lifetime
- 1997-09-24 ES ES97202917T patent/ES2221679T3/es not_active Expired - Lifetime
- 1997-09-24 AT AT97202917T patent/ATE267179T1/de not_active IP Right Cessation
- 1997-09-25 CA CA002216486A patent/CA2216486A1/en not_active Abandoned
- 1997-09-26 US US08/938,602 patent/US6380194B1/en not_active Expired - Fee Related
- 1997-09-26 AU AU39266/97A patent/AU740809B2/en not_active Ceased
- 1997-09-26 EE EE9700253A patent/EE03826B1/xx not_active IP Right Cessation
- 1997-09-26 NZ NZ328854A patent/NZ328854A/xx unknown
- 1997-09-29 IL IL12184997A patent/IL121849A/xx not_active IP Right Cessation
- 1997-09-29 KR KR1019970049662A patent/KR100478846B1/ko not_active IP Right Cessation
- 1997-09-29 MY MYPI97004540A patent/MY123803A/en unknown
- 1997-09-29 ID IDP973312A patent/ID19599A/id unknown
- 1997-09-29 JP JP27938797A patent/JP4127882B2/ja not_active Expired - Fee Related
- 1997-09-29 SK SK1319-97A patent/SK285241B6/sk unknown
- 1997-09-29 AP APAP/P/1997/001109A patent/AP914A/en active
- 1997-09-30 ZA ZA978766A patent/ZA978766B/xx unknown
- 1997-09-30 BR BR9704937-9A patent/BR9704937A/pt not_active Application Discontinuation
- 1997-09-30 RU RU97116200/04A patent/RU2186774C2/ru not_active IP Right Cessation
- 1997-09-30 TW TW086114172A patent/TW411335B/zh not_active IP Right Cessation
- 1997-09-30 HU HU9701596A patent/HU225270B1/hu not_active IP Right Cessation
- 1997-09-30 CN CN97121454A patent/CN1083438C/zh not_active Expired - Fee Related
- 1997-09-30 HR HR970526A patent/HRP970526B1/xx not_active IP Right Cessation
- 1997-09-30 TR TR97/01070A patent/TR199701070A2/xx unknown
- 1997-09-30 AR ARP970104503A patent/AR008864A1/es active IP Right Grant
- 1997-09-30 PL PL97322369A patent/PL190155B1/pl not_active IP Right Cessation
- 1997-10-01 OA OA70094A patent/OA10620A/en unknown
-
1998
- 1998-09-09 HK HK98110540A patent/HK1009676A1/xx not_active IP Right Cessation
-
2001
- 2001-11-15 US US10/002,456 patent/US6858609B2/en not_active Expired - Fee Related
-
2003
- 2003-03-26 US US10/397,760 patent/US6962916B2/en not_active Expired - Fee Related
-
2005
- 2005-08-12 US US11/203,325 patent/US7449575B2/en not_active Expired - Fee Related
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