SK287269B6 - Derivát pyrimidínu, jeho použitie, spôsob jeho prípravy a farmaceutická kompozícia, kombinácia a produkt s jeho obsahom - Google Patents

Derivát pyrimidínu, jeho použitie, spôsob jeho prípravy a farmaceutická kompozícia, kombinácia a produkt s jeho obsahom Download PDF

Info

Publication number: SK287269B6
Authority: SK; Slovakia
Prior art keywords: alkyl; amino; cyano; formula; pyrimidine derivative
Prior art date: 1998-11-10

Application number

SK603-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK6032001A3 (en

Inventor

Corte Bart De

Jonge Marc Ren De

Jan Heeres

Chih Yung Ho

Paul Adriaan Jan Janssen

Robert W. Kavash

Lucien Maria Henricus Koymans

Michael Joseph Kukla

Donald William Ludovici

Aken Koen Jeanne Alfons Van

Koenraad Jozef Lodewijk Marcel Andries

Original Assignee

Janssen Pharmaceutica N. V.

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.)

1998-11-10

Filing date

1999-09-24

Publication date

2010-05-07

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26805159&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK287269(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-09-24 Application filed by Janssen Pharmaceutica N. V. filed Critical Janssen Pharmaceutica N. V.

2002-01-07 Publication of SK6032001A3 publication Critical patent/SK6032001A3/sk

2010-05-07 Publication of SK287269B6 publication Critical patent/SK287269B6/sk

Links

150000003230 pyrimidines Chemical class 0.000 title claims abstract description 30
238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 18
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
230000008569 process Effects 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 110
150000003839 salts Chemical class 0.000 claims abstract description 33
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 25
239000003814 drug Substances 0.000 claims abstract description 14
150000001204 N-oxides Chemical class 0.000 claims abstract description 13
230000000798 anti-retroviral effect Effects 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 6
150000001412 amines Chemical group 0.000 claims abstract description 4
208000015181 infectious disease Diseases 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 80
-1 cyano, aminocarbonyl Chemical group 0.000 claims description 80
239000000460 chlorine Substances 0.000 claims description 65
239000002904 solvent Substances 0.000 claims description 57
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 38
125000004093 cyano group Chemical group *C#N 0.000 claims description 37
229910052736 halogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 32
125000003118 aryl group Chemical group 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
239000002585 base Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000012298 atmosphere Substances 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000002098 pyridazinyl group Chemical group 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
GNELAKVSOPMFKN-UHFFFAOYSA-N 4-[5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Br GNELAKVSOPMFKN-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 6
VKQKEROEGYSHIY-UHFFFAOYSA-N 4-[[5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]amino]-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Br VKQKEROEGYSHIY-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
230000009385 viral infection Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 77
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
239000000543 intermediate Substances 0.000 description 42
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 32
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 26
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
229920000858 Cyclodextrin Polymers 0.000 description 21
239000007787 solid Substances 0.000 description 19
229910052786 argon Inorganic materials 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
239000003480 eluent Substances 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 13
238000002390 rotary evaporation Methods 0.000 description 13
239000000725 suspension Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
229940097362 cyclodextrins Drugs 0.000 description 9
238000002953 preparative HPLC Methods 0.000 description 9
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 8
229940126657 Compound 17 Drugs 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
150000002430 hydrocarbons Chemical group 0.000 description 8
239000000463 material 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 7
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
238000001914 filtration Methods 0.000 description 7
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125000006239 protecting group Chemical group 0.000 description 7
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
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238000004440 column chromatography Methods 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 6
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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 5
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ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
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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
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ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035899 viability Effects 0.000 description 1
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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
- 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
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- 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
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Virology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Tropical Medicine & Parasitology (AREA)
AIDS & HIV (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK603-2001A 1998-11-10 1999-09-24 Derivát pyrimidínu, jeho použitie, spôsob jeho prípravy a farmaceutická kompozícia, kombinácia a produkt s jeho obsahom SK287269B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US10779298P	1998-11-10	1998-11-10
US14396299P	1999-07-15	1999-07-15
PCT/EP1999/007417 WO2000027825A1 (en)	1998-11-10	1999-09-24	Hiv replication inhibiting pyrimidines

Publications (2)

Publication Number	Publication Date
SK6032001A3 SK6032001A3 (en)	2002-01-07
SK287269B6 true SK287269B6 (sk)	2010-05-07

Family

ID=26805159

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SK603-2001A SK287269B6 (sk)	1998-11-10	1999-09-24	Derivát pyrimidínu, jeho použitie, spôsob jeho prípravy a farmaceutická kompozícia, kombinácia a produkt s jeho obsahom
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1999
- 1999-09-24 KR KR1020017003576A patent/KR100658489B1/ko not_active Expired - Lifetime
- 1999-09-24 AP APAP/P/2001/002121A patent/AP1683A/en active
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- 1999-09-24 WO PCT/EP1999/007417 patent/WO2000027825A1/en not_active Ceased
- 1999-09-24 HR HRP20010161AA patent/HRP20010161B9/hr not_active IP Right Cessation
- 1999-09-24 SK SK603-2001A patent/SK287269B6/sk active Protection Beyond IP Right Term
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- 1999-09-24 ID IDW00200101015A patent/ID28376A/id unknown
- 1999-09-24 EE EEP200100252A patent/EE05086B1/xx active Protection Beyond IP Right Term
- 1999-09-24 CZ CZ20011533A patent/CZ301367B6/cs not_active IP Right Cessation
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- 1999-09-24 UA UA2001042857A patent/UA70966C2/uk unknown
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- 1999-11-01 DK DK99203590T patent/DK1002795T3/da active
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- 1999-11-01 SI SI9930275T patent/SI1002795T1/xx unknown
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2001
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- 2001-04-06 BG BG105418A patent/BG65103B1/bg unknown
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2003
- 2003-02-14 HK HK03101063.7A patent/HK1048817B/en not_active IP Right Cessation
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2005
- 2005-07-28 IL IL169949A patent/IL169949A/en not_active IP Right Cessation
- 2005-08-16 US US11/204,513 patent/US20050288278A1/en not_active Abandoned
2007
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2008
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2009
- 2009-01-13 NL NL300373C patent/NL300373I2/nl unknown
- 2009-01-22 FR FR09C0004C patent/FR09C0004I2/fr active Active
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2011
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Also Published As

Publication number	Publication date
UA70966C2 (uk)	2004-11-15
DE69941934D1 (de)	2010-03-04
LTC1002795I2 (lt)	2021-06-10
NO318801B1 (no)	2005-05-09
US8530655B2 (en)	2013-09-10
LTPA2008016I1 (lt)	2021-04-26
LU91528I2 (fr)	2009-04-20
NL300373I1 (nl)	2009-03-02
LU91528I9 (es)	2019-01-02
HRP20010161B1 (en)	2009-03-31
EE200100252A (et)	2002-10-15
DE69905683D1 (de)	2003-04-10
DK1002795T3 (da)	2003-06-30
NL300373I2 (nl)	2009-04-01
SK287270B6 (sk)	2010-05-07
US20030114472A1 (en)	2003-06-19
NO2021015I1 (no)	2021-03-29
EP1270560B1 (en)	2010-01-13
HUP0104177A2 (hu)	2002-03-28
EP1002795B1 (en)	2003-03-05
US8003789B2 (en)	2011-08-23
KR100658489B1 (ko)	2006-12-18
PL204427B1 (pl)	2010-01-29
BG105418A (en)	2001-11-30
SK6032001A3 (en)	2002-01-07
HU227453B1 (en)	2011-06-28
DE122009000003I1 (de)	2009-05-20
OA11674A (en)	2005-01-12
HK1048817B (en)	2010-04-09
ATE233740T1 (de)	2003-03-15
EP1270560A1 (en)	2003-01-02
AU762523B2 (en)	2003-06-26
BRPI9915552B8 (pt)	2021-05-25
BR9915552A (pt)	2001-08-14
US6878717B2 (en)	2005-04-12
EA200100536A1 (ru)	2002-02-28
EP1002795A1 (en)	2000-05-24
HRP20080359A2 (en)	2008-12-31
NZ511116A (en)	2003-08-29
CN1322198A (zh)	2001-11-14
NO20011696D0 (no)	2001-04-04
AU762523C (en)	2004-02-12
HU230394B1 (hu)	2016-04-28
CA2350801A1 (en)	2000-05-18
EA004049B1 (ru)	2003-12-25
ZA200103769B (en)	2002-08-12
IL169949A (en)	2011-02-28
SI1002795T1 (en)	2003-10-31
PL347586A1 (en)	2002-04-08
NO2009003I1 (no)	2009-03-09
HUP0104177A3 (en)	2003-01-28
NO2009003I2 (no)	2010-06-07
IL143023A0 (en)	2002-04-21
MY121108A (en)	2005-12-30
US7037917B2 (en)	2006-05-02
ES2338760T3 (es)	2010-05-12
CA2350801C (en)	2008-05-20
AU6200899A (en)	2000-05-29
CY2008021I2 (el)	2010-07-28
DE69905683T2 (de)	2004-03-18
ID28376A (id)	2001-05-17
NO20011696L (no)	2001-04-04
KR20010075235A (ko)	2001-08-09
BG65103B1 (bg)	2007-02-28
CY2008021I1 (el)	2010-07-28
US20040039005A1 (en)	2004-02-26
CN1214013C (zh)	2005-08-10
CZ301367B6 (cs)	2010-02-03
CZ20011533A3 (cs)	2001-10-17
PT1002795E (pt)	2003-07-31
HK1048817A1 (en)	2003-04-17
AR024227A1 (es)	2002-09-25
JP3635238B2 (ja)	2005-04-06
HRP20010161B9 (hr)	2014-10-24
HRP20010161A2 (en)	2002-02-28
AU2011200708A1 (en)	2011-03-10
WO2000027825A1 (en)	2000-05-18
EE05086B1 (et)	2008-10-15
US20110263625A1 (en)	2011-10-27
ES2193664T3 (es)	2003-11-01
ATE455107T1 (de)	2010-01-15
JP2002529456A (ja)	2002-09-10
US20080176880A1 (en)	2008-07-24
US20050288278A1 (en)	2005-12-29
TR200101306T2 (tr)	2001-10-22
HRP20080359B1 (hr)	2016-01-01
FR09C0004I2 (fr)	2010-06-11
HK1025330A1 (en)	2000-11-10
TWI238161B (en)	2005-08-21
FR09C0004I1 (es)	2009-02-27
BR9915552B1 (pt)	2013-11-19
AP1683A (en)	2006-11-29

Publication	Publication Date	Title
SK287269B6 (sk)	2010-05-07	Derivát pyrimidínu, jeho použitie, spôsob jeho prípravy a farmaceutická kompozícia, kombinácia a produkt s jeho obsahom
DK1282607T3 (en)	2016-02-01	Prodrugs of HIV replication inhibiting pyrimidines
BG65754B1 (bg)	2009-10-30	Антивирусни състави
AU5633301A (en)	2001-11-20	Hiv replication inhibitors
HK1025330B (en)	2003-06-13	Hiv replication inhibiting pyrimidines
MXPA01003646A (es)	2001-12-04	Pirimidinas inhibidoras de replicacion del virus de inmunodeficiencia humana

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