OA10620A - Substituted diamino-1, 3, 5-triazine derivatives - Google Patents

Substituted diamino-1, 3, 5-triazine derivatives Download PDF

Info

Publication number: OA10620A
Authority: OA; OAPI
Prior art keywords: formula; amino; compound; 6alkyl; phenyl
Prior art date: 1996-10-01

Application number

OA70094A

Other languages

English (en)

Inventor

Michael Jpseph Kukla

Donald W Ludovici

Paul Adriaan Jan Janssen

Jan Heeres

Henri Emiel Lodewijk Moereels

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-10-01

Filing date

1997-10-01

Publication date

2002-09-03

1997-10-01 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2002-09-03 Publication of OA10620A publication Critical patent/OA10620A/en

Links

VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 144
-1 C1-6alkyloxycarbonyl Chemical group 0.000 claims abstract description 130
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 47
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
239000001257 hydrogen Substances 0.000 claims abstract description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 23
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 23
239000002253 acid Substances 0.000 claims abstract description 19
150000002431 hydrogen Chemical class 0.000 claims abstract description 17
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 11
238000011282 treatment Methods 0.000 claims abstract description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 9
238000004519 manufacturing process Methods 0.000 claims abstract description 6
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 5
208000015181 infectious disease Diseases 0.000 claims abstract description 5
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
125000001475 halogen functional group Chemical group 0.000 claims abstract 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
239000012442 inert solvent Substances 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000001041 indolyl group Chemical group 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
230000036436 anti-hiv Effects 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
239000002585 base Substances 0.000 claims 3
239000003513 alkali Substances 0.000 claims 1
125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 32
150000003839 salts Chemical class 0.000 abstract description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
229910052786 argon Inorganic materials 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000000460 chlorine Substances 0.000 description 17
125000005843 halogen group Chemical group 0.000 description 17
239000007787 solid Substances 0.000 description 17
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
238000000034 method Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
210000004027 cell Anatomy 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
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239000003826 tablet Substances 0.000 description 6
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 5
229960004132 diethyl ether Drugs 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
235000015320 potassium carbonate Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
208000031886 HIV Infections Diseases 0.000 description 4
208000037357 HIV infectious disease Diseases 0.000 description 4
241000713772 Human immunodeficiency virus 1 Species 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
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
206010001513 AIDS related complex Diseases 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
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235000019439 ethyl acetate Nutrition 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
241001430294 unidentified retrovirus Species 0.000 description 3
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
OXTFFPWHLJQPEE-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)ethanimidamide Chemical compound NC(=N)CC1=C(Cl)C=CC=C1Cl OXTFFPWHLJQPEE-UHFFFAOYSA-N 0.000 description 2
VVYNPLKGRWZKRS-UHFFFAOYSA-N 2-(2-anilinophenyl)acetamide Chemical compound NC(=O)CC1=CC=CC=C1NC1=CC=CC=C1 VVYNPLKGRWZKRS-UHFFFAOYSA-N 0.000 description 2
AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
206010012289 Dementia Diseases 0.000 description 2
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
241000700605 Viruses Species 0.000 description 2
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230000003110 anti-inflammatory effect Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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XSQUKJJJFZCRTK-UHFFFAOYSA-M carbamimidate Chemical compound NC([NH-])=O XSQUKJJJFZCRTK-UHFFFAOYSA-M 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
229940126208 compound 22 Drugs 0.000 description 2
229960002656 didanosine Drugs 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
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 2
150000004677 hydrates Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000001717 pathogenic effect Effects 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000006187 pill Substances 0.000 description 2
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
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JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 description 2
229960002555 zidovudine Drugs 0.000 description 2
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
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Classifications

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- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- 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
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- 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)
Virology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Tropical Medicine & Parasitology (AREA)
AIDS & HIV (AREA)
Bioinformatics & Cheminformatics (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)

OA70094A 1996-10-01 1997-10-01 Substituted diamino-1, 3, 5-triazine derivatives OA10620A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2726096P	1996-10-01	1996-10-01

Publications (1)

Publication Number	Publication Date
OA10620A true OA10620A (en)	2002-09-03

Family

ID=21836641

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Application Number	Title	Priority Date	Filing Date
OA70094A OA10620A (en)	1996-10-01	1997-10-01	Substituted diamino-1, 3, 5-triazine derivatives

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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)
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)

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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 DK DK97202917T patent/DK0834507T3/da active
- 1997-09-24 PT PT97202917T patent/PT834507E/pt unknown
- 1997-09-24 DE DE69729153T patent/DE69729153T2/de not_active Expired - Fee Related
- 1997-09-24 EP EP97202917A patent/EP0834507B1/en not_active Expired - Lifetime
- 1997-09-24 AT AT97202917T patent/ATE267179T1/de not_active IP Right Cessation
- 1997-09-24 SI SI9730663T patent/SI0834507T1/xx unknown
- 1997-09-24 ES ES97202917T patent/ES2221679T3/es not_active Expired - Lifetime
- 1997-09-25 CA CA002216486A patent/CA2216486A1/en not_active Abandoned
- 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
- 1997-09-26 US US08/938,602 patent/US6380194B1/en not_active Expired - Fee Related
- 1997-09-29 JP JP27938797A patent/JP4127882B2/ja not_active Expired - Fee Related
- 1997-09-29 KR KR1019970049662A patent/KR100478846B1/ko not_active Expired - Fee Related
- 1997-09-29 ID IDP973312A patent/ID19599A/id unknown
- 1997-09-29 AP APAP/P/1997/001109A patent/AP914A/en active
- 1997-09-29 MY MYPI97004540A patent/MY123803A/en unknown
- 1997-09-29 SK SK1319-97A patent/SK285241B6/sk unknown
- 1997-09-29 IL IL12184997A patent/IL121849A/xx not_active IP Right Cessation
- 1997-09-30 PL PL97322369A patent/PL190155B1/pl not_active IP Right Cessation
- 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 HR HR970526A patent/HRP970526B1/xx not_active IP Right Cessation
- 1997-09-30 ZA ZA978766A patent/ZA978766B/xx unknown
- 1997-09-30 AR ARP970104503A patent/AR008864A1/es active IP Right Grant
- 1997-09-30 HU HU9701596A patent/HU225270B1/hu not_active IP Right Cessation
- 1997-09-30 TW TW086114172A patent/TW411335B/zh not_active IP Right Cessation
- 1997-09-30 CN CN97121454A patent/CN1083438C/zh not_active Expired - Fee Related
- 1997-09-30 TR TR97/01070A patent/TR199701070A2/xx unknown
- 1997-10-01 OA OA70094A patent/OA10620A/en unknown
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
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Also Published As

Publication number	Publication date
CZ299397A3 (cs)	1998-11-11
AU740809B2 (en)	2001-11-15
SG53075A1 (en)	1998-09-28
HUP9701596A2 (hu)	1999-06-28
CZ297333B6 (cs)	2006-11-15
EE9700253A (et)	1998-04-15
US20030199473A1 (en)	2003-10-23
SK131997A3 (en)	1999-06-11
AU3926697A (en)	1998-04-09
HUP9701596A3 (en)	2000-04-28
TR199701070A2 (xx)	1998-04-21
NO311614B1 (no)	2001-12-17
KR100478846B1 (ko)	2006-06-13
PT834507E (pt)	2004-10-29
ZA978766B (en)	1999-03-30
DK0834507T3 (da)	2004-09-06
CN1083438C (zh)	2002-04-24
IL121849A0 (en)	1998-02-22
NZ328854A (en)	2000-10-27
MX9707511A (es)	1998-06-30
PL190155B1 (pl)	2005-11-30
HK1009676A1 (en)	1999-06-04
SK285241B6 (sk)	2006-09-07
ES2221679T3 (es)	2005-01-01
AR008864A1 (es)	2000-02-23
ID19599A (id)	1998-07-23
EE03826B1 (et)	2002-08-15
DE69729153D1 (de)	2004-06-24
HU225270B1 (en)	2006-08-28
US7449575B2 (en)	2008-11-11
KR19980032428A (ko)	1998-07-25
PL322369A1 (en)	1998-04-14
IL121849A (en)	2001-08-26
TW411335B (en)	2000-11-11
DE69729153T2 (de)	2005-01-27
MY123803A (en)	2006-06-30
ATE267179T1 (de)	2004-06-15
EP0834507B1 (en)	2004-05-19
CN1180698A (zh)	1998-05-06
HRP970526B1 (en)	2002-10-31
JPH10114759A (ja)	1998-05-06
US6962916B2 (en)	2005-11-08
HU9701596D0 (en)	1997-11-28
NO974368L (no)	1998-04-02
JP4127882B2 (ja)	2008-07-30
NO974368D0 (no)	1997-09-22
SI0834507T1 (en)	2004-10-31
US20020147181A1 (en)	2002-10-10
US20060189614A1 (en)	2006-08-24
RU2186774C2 (ru)	2002-08-10
EP0834507A1 (en)	1998-04-08
HRP970526A2 (en)	1998-10-31
AP914A (en)	2000-12-18
BR9704937A (pt)	2000-06-06
US6858609B2 (en)	2005-02-22
US6380194B1 (en)	2002-04-30
AP9701109A0 (en)	1997-10-31
CA2216486A1 (en)	1998-04-01

Publication	Publication Date	Title
OA10620A (en)	2002-09-03	Substituted diamino-1, 3, 5-triazine derivatives
US20060049177A1 (en)	2006-03-09	Induction heating cooker
US6372729B1 (en)	2002-04-16	Trisubstituted 1,3,5,-triazine derivatives
CA2324919C (en)	2006-10-17	Hiv inhibiting pyrimidine derivatives
ES2361146T3 (es)	2011-06-14	Derivados de la piramidina inhibitatoria de vih.
EP0945442A1 (en)	1999-09-29	Trisubstituted pyrimidine derivatives
HK1009676B (en)	2004-10-29	Substituted diamino-1,3,5-triazine derivatives
HK1032394B (en)	2005-10-21	Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections
MXPA97007511A (en)	1998-10-30	Derivatives of diamino-1,3,5-triazina substituted, its preparation, compositions that contain them and the use of the mis