OA13079A - Pre-organized tricyclic integrase inhibitor compounds. - Google Patents

Pre-organized tricyclic integrase inhibitor compounds. Download PDF

Info

Publication number: OA13079A
Authority: OA; OAPI
Prior art keywords: compound; phosphonate; substituted; aryl; heteroaryl
Prior art date: 2002-10-16

Application number

OA1200500108A

Other languages

English (en)

Inventor

James M Chen

Xiaowu Chen

Maria Fardis

Haolun Jin

Choung U Kim

Laura N Schacherer

Original Assignee

Gilead Sciences Inc

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.)

2002-10-16

Filing date

2003-10-16

Publication date

2006-11-10

2003-10-16 Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc

2006-11-10 Publication of OA13079A publication Critical patent/OA13079A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 277
229940124524 integrase inhibitor Drugs 0.000 title claims description 8
239000002850 integrase inhibitor Substances 0.000 title claims description 8
238000000034 method Methods 0.000 claims abstract description 242
239000000651 prodrug Substances 0.000 claims abstract description 91
229940002612 prodrug Drugs 0.000 claims abstract description 91
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 81
125000003118 aryl group Chemical group 0.000 claims abstract description 74
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 67
229910052717 sulfur Inorganic materials 0.000 claims abstract description 47
229910052760 oxygen Inorganic materials 0.000 claims abstract description 43
125000001424 substituent group Chemical group 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 198
-1 polyethyleneoxy Polymers 0.000 claims description 162
238000006243 chemical reaction Methods 0.000 claims description 146
239000000203 mixture Substances 0.000 claims description 112
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 92
150000001412 amines Chemical class 0.000 claims description 58
150000002148 esters Chemical class 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 47
229910052799 carbon Inorganic materials 0.000 claims description 47
125000002947 alkylene group Chemical group 0.000 claims description 37
125000006239 protecting group Chemical group 0.000 claims description 29
239000003795 chemical substances by application Substances 0.000 claims description 25
229910019142 PO4 Inorganic materials 0.000 claims description 24
125000000547 substituted alkyl group Chemical group 0.000 claims description 24
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 24
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 23
239000010452 phosphate Substances 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 21
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000003153 chemical reaction reagent Substances 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 16
150000003951 lactams Chemical class 0.000 claims description 16
125000003107 substituted aryl group Chemical group 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 14
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000004419 alkynylene group Chemical group 0.000 claims description 11
239000003112 inhibitor Substances 0.000 claims description 11
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 11
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 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
102100034343 Integrase Human genes 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 8
150000001350 alkyl halides Chemical class 0.000 claims description 8
150000008052 alkyl sulfonates Chemical class 0.000 claims description 8
150000007942 carboxylates Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
230000003834 intracellular effect Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
108010061833 Integrases Proteins 0.000 claims description 7
150000001356 alkyl thiols Chemical class 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
229960002317 succinimide Drugs 0.000 claims description 6
229940124530 sulfonamide Drugs 0.000 claims description 6
150000003456 sulfonamides Chemical class 0.000 claims description 6
125000004950 trifluoroalkyl group Chemical group 0.000 claims description 6
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
229910019946 S-S Inorganic materials 0.000 claims description 5
229910019939 S—S Inorganic materials 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 5
208000030507 AIDS Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000002243 precursor Substances 0.000 claims description 4
229940099797 HIV integrase inhibitor Drugs 0.000 claims description 3
239000004599 antimicrobial Substances 0.000 claims description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
239000003084 hiv integrase inhibitor Substances 0.000 claims description 3
150000002596 lactones Chemical class 0.000 claims description 3
239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 3
150000003457 sulfones Chemical class 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
230000008685 targeting Effects 0.000 claims description 3
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
229940122440 HIV protease inhibitor Drugs 0.000 claims description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 claims description 2
229960005475 antiinfective agent Drugs 0.000 claims description 2
239000004030 hiv protease inhibitor Substances 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
239000002955 immunomodulating agent Substances 0.000 claims description 2
229940121354 immunomodulator Drugs 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 17
210000000265 leukocyte Anatomy 0.000 claims 4
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
230000002584 immunomodulator Effects 0.000 claims 1
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims 1
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims 1
230000002194 synthesizing effect Effects 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 133
239000000543 intermediate Substances 0.000 abstract description 24
125000006413 ring segment Chemical group 0.000 abstract description 12
108010002459 HIV Integrase Proteins 0.000 abstract description 11
230000005764 inhibitory process Effects 0.000 abstract description 7
150000002829 nitrogen Chemical class 0.000 abstract description 3
239000000047 product Substances 0.000 description 284
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 274
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 223
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 196
239000000243 solution Substances 0.000 description 149
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 130
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 126
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 115
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
238000005481 NMR spectroscopy Methods 0.000 description 82
235000019439 ethyl acetate Nutrition 0.000 description 76
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 73
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 64
229920006395 saturated elastomer Polymers 0.000 description 60
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 57
238000010511 deprotection reaction Methods 0.000 description 56
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 54
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
229940093499 ethyl acetate Drugs 0.000 description 43
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
239000002585 base Substances 0.000 description 42
239000002253 acid Substances 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
229940086542 triethylamine Drugs 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 36
229910000041 hydrogen chloride Inorganic materials 0.000 description 36
238000004809 thin layer chromatography Methods 0.000 description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 35
239000007787 solid Substances 0.000 description 35
239000002904 solvent Substances 0.000 description 34
239000007858 starting material Substances 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
238000009472 formulation Methods 0.000 description 31
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
229910001868 water Inorganic materials 0.000 description 31
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 29
239000003039 volatile agent Substances 0.000 description 29
150000005690 diesters Chemical class 0.000 description 28
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
125000003710 aryl alkyl group Chemical group 0.000 description 27
229910000027 potassium carbonate Inorganic materials 0.000 description 27
229960004132 diethyl ether Drugs 0.000 description 26
150000001408 amides Chemical class 0.000 description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
229940116254 phosphonic acid Drugs 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000012043 crude product Substances 0.000 description 24
230000002829 reductive effect Effects 0.000 description 24
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
230000003197 catalytic effect Effects 0.000 description 22
125000004122 cyclic group Chemical group 0.000 description 21
239000011734 sodium Substances 0.000 description 21
239000003814 drug Substances 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000012044 organic layer Substances 0.000 description 19
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 18
125000002015 acyclic group Chemical group 0.000 description 17
229940079593 drug Drugs 0.000 description 17
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 16
150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
150000003009 phosphonic acids Chemical class 0.000 description 16
229940093956 potassium carbonate Drugs 0.000 description 16
235000011181 potassium carbonates Nutrition 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
210000004027 cell Anatomy 0.000 description 15
238000005859 coupling reaction Methods 0.000 description 15
239000003921 oil Substances 0.000 description 15
239000012267 brine Substances 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
235000021317 phosphate Nutrition 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 13
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 13
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 13
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 13
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 13
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
235000011054 acetic acid Nutrition 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 12
238000006460 hydrolysis reaction Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
229960001866 silicon dioxide Drugs 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
238000006073 displacement reaction Methods 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
125000005647 linker group Chemical group 0.000 description 11
235000015320 potassium carbonate Nutrition 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
239000000376 reactant Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000012279 sodium borohydride Substances 0.000 description 11
229910000033 sodium borohydride Inorganic materials 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
150000003568 thioethers Chemical class 0.000 description 11
230000009466 transformation Effects 0.000 description 11
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 10
230000008878 coupling Effects 0.000 description 10
238000010168 coupling process Methods 0.000 description 10
150000002440 hydroxy compounds Chemical class 0.000 description 10
239000000463 material Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
238000007363 ring formation reaction Methods 0.000 description 10
238000000844 transformation Methods 0.000 description 10
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
150000008064 anhydrides Chemical class 0.000 description 9
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 9
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
229910052763 palladium Inorganic materials 0.000 description 9
239000002798 polar solvent Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 9
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
238000005804 alkylation reaction Methods 0.000 description 8
150000007854 aminals Chemical class 0.000 description 8
230000000840 anti-viral effect Effects 0.000 description 8
150000001718 carbodiimides Chemical class 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
ROBXZHNBBCHEIQ-BYPYZUCNSA-N ethyl (2s)-2-aminopropanoate Chemical compound CCOC(=O)[C@H](C)N ROBXZHNBBCHEIQ-BYPYZUCNSA-N 0.000 description 8
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
125000005842 heteroatom Chemical group 0.000 description 8
150000007857 hydrazones Chemical class 0.000 description 8
208000015181 infectious disease Diseases 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
239000002777 nucleoside Substances 0.000 description 8
239000012071 phase Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
241000700605 Viruses Species 0.000 description 7
125000004450 alkenylene group Chemical group 0.000 description 7
230000031709 bromination Effects 0.000 description 7
238000005893 bromination reaction Methods 0.000 description 7
125000004185 ester group Chemical group 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
239000012442 inert solvent Substances 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
239000007788 liquid Substances 0.000 description 7
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
239000003495 polar organic solvent Substances 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
150000003573 thiols Chemical class 0.000 description 7
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MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
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LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
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125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 1
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150000003553 thiiranes Chemical class 0.000 description 1
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LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=O)N[C@H](CO)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](CO)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(O)=O)C(O)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 description 1
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OKKJLVBELUTLKV-FIBGUPNXSA-N trideuteriomethanol Chemical compound [2H]C([2H])([2H])O OKKJLVBELUTLKV-FIBGUPNXSA-N 0.000 description 1
VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
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OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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AUFUWRKPQLGTGF-FMKGYKFTSA-N uridine triacetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=C1 AUFUWRKPQLGTGF-FMKGYKFTSA-N 0.000 description 1
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UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
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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 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems

Landscapes

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

OA1200500108A 2002-10-16 2003-10-16 Pre-organized tricyclic integrase inhibitor compounds. OA13079A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US41896302P	2002-10-16	2002-10-16
US47878303P	2003-06-16	2003-06-16

Publications (1)

Publication Number	Publication Date
OA13079A true OA13079A (en)	2006-11-10

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ID=32110203

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Application Number	Title	Priority Date	Filing Date
OA1200500108A OA13079A (en)	2002-10-16	2003-10-16	Pre-organized tricyclic integrase inhibitor compounds.

Country Status (19)

Country	Link
US (3)	US20040157804A1 (is)
EP (1)	EP1558613A2 (is)
JP (1)	JP2006514099A (is)
KR (1)	KR20050087787A (is)
CN (1)	CN100374438C (is)
AP (1)	AP1858A (is)
AU (2)	AU2003301439A1 (is)
BR (1)	BR0315405A (is)
CA (1)	CA2501881A1 (is)
EA (1)	EA011399B1 (is)
HR (1)	HRP20050431A2 (is)
IS (1)	IS7845A (is)
MX (1)	MXPA05003950A (is)
NO (1)	NO20052378L (is)
NZ (1)	NZ539264A (is)
OA (1)	OA13079A (is)
PL (1)	PL377966A1 (is)
UA (1)	UA79830C2 (is)
WO (2)	WO2004035577A2 (is)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE420636T1 (de) *	1999-05-19	2009-01-15	Painceptor Pharma Corp	Hemmer der protonenabhängigen kationenkanäle und deren verwendung in der behandlung von ischemiebedingten erkrankungen
EP1625130A2 (en) *	2003-04-28	2006-02-15	Tibotec Pharmaceuticals Ltd.	Hiv integrase inhibitors
ATE433974T1 (de)	2003-09-19	2009-07-15	Gilead Sciences Inc	Azachinolinolphosphonatverbindungen als integraseinhibitoren
JP4804361B2 (ja) *	2003-12-08	2011-11-02	ザリサーチファウンデイションオブステイトユニバーシティーオブニューヨーク	センサー利用のための、部位選択的にタグ付および鋳造された分子インプリントポリマー
US7572914B2 (en)	2003-12-19	2009-08-11	Takeda Pharmaceutical Company Limited	Kinase inhibitors
EP1706728A4 (en) *	2004-01-07	2008-03-12	Univ New York State Res Found	PROTEIN IMPREGNATED POLYMERS WITH INTEGRATED TRANSMISSION SITES
PL1742642T3 (pl) *	2004-04-14	2009-06-30	Gilead Sciences Inc	Analogi fosfonianowe związków inhibitorów integrazy HIV
JP4824673B2 (ja) *	2004-05-07	2011-11-30	メルク・シャープ・エンド・ドーム・コーポレイション	Ｈｉｖインテグラーゼ阻害剤
CA2568389A1 (en) *	2004-06-09	2005-12-22	Merck & Co., Inc.	Hiv integrase inhibitors
WO2006023931A2 (en)	2004-08-18	2006-03-02	Takeda San Diego, Inc.	Kinase inhibitors
US7745459B2 (en)	2004-09-21	2010-06-29	Japan Tobacco Inc.	Quinolizinone compound and use thereof as HIV integrase inhibitor
US7713973B2 (en)	2004-10-15	2010-05-11	Takeda Pharmaceutical Company Limited	Kinase inhibitors
AR057023A1 (es) *	2005-05-16	2007-11-14	Gilead Sciences Inc	Compuestos heterociclicos con propiedades inhibidoras de hiv-integrasa
ATE533766T1 (de)	2005-05-19	2011-12-15	Merck Canada Inc	Chinolinderivate als ep4-antagonisten
JP2009502964A (ja) *	2005-07-27	2009-01-29	ギリアードサイエンシーズ，インコーポレイテッド	Ｈｉｖを阻害するための抗ウイルス性ホスホン酸結合体
US20080234231A1 (en) *	2005-08-04	2008-09-25	Johns Brian A	Hiv Integrase Inhibitors
US8119655B2 (en)	2005-10-07	2012-02-21	Takeda Pharmaceutical Company Limited	Kinase inhibitors
WO2007076005A2 (en) *	2005-12-21	2007-07-05	Gilead Sciences, Inc.	Processes and intermediates useful for preparing integrase inhibitor compounds
US20090233964A1 (en) *	2005-12-30	2009-09-17	Gilead Sciences, Inc.	Methods for improving the pharmacokinetics of hiv integrase inhibitors
AP2702A (en)	2005-12-30	2013-07-23	Gilead Sciences Inc	Methods for improving the pharmacokinetics of HIV integrase inhibitors
NZ572367A (en) *	2006-05-16	2011-09-30	Gilead Sciences Inc	Fused cyclic compounds as integrase inhibitors
GEP20135728B (en)	2006-10-09	2013-01-25	Takeda Pharmaceuticals Co	Kinase inhibitors
WO2009067541A2 (en) *	2007-11-20	2009-05-28	Gilead Sciences, Inc.	Integrase inhibitors
AU2009206673B2 (en)	2008-01-25	2015-04-23	Chimerix, Inc.	Methods of treating viral infections
PT2660239T (pt)	2008-07-25	2017-02-24	Shionogi & Co	Compostos químicos como intermediários sintéticos
MX2011000971A (es) *	2008-07-28	2011-06-24	Polymedix Inc	Compuestos antipaludicos.
MX351942B (es)	2008-12-11	2017-11-03	Shionogi & Co	Sintesis de inhibidores de integrasa de vih de carbamoil-piridona e intermediarios.
EP2376453B1 (en)	2008-12-11	2019-11-20	VIIV Healthcare Company	Intermediates for carbamoylpyridone hiv integrase inhibitors
TWI518084B (zh)	2009-03-26	2016-01-21	鹽野義製藥股份有限公司	哌喃酮與吡啶酮衍生物之製造方法
EP2270021A1 (en) *	2009-06-18	2011-01-05	Centre National de la Recherche Scientifique	Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability
WO2011011483A1 (en) *	2009-07-22	2011-01-27	Glaxosmithkline Llc	Chemical compounds
NZ598766A (en)	2009-10-13	2013-09-27	Elanco Animal Health Ireland	Macrocyclic integrase inhibitors
US8283366B2 (en)	2010-01-22	2012-10-09	Ambrilia Biopharma, Inc.	Derivatives of pyridoxine for inhibiting HIV integrase
JP5745869B2 (ja) *	2010-01-22	2015-07-08	富山化学工業株式会社	アルアルキル基を有する複素環化合物
EP3216789A1 (en)	2010-02-12	2017-09-13	Chimerix, Inc.	Methods of treating viral infection
TWI582097B (zh)	2010-03-23	2017-05-11	Ｖｉｉｖ醫療保健公司	製備胺甲醯吡啶酮衍生物及中間體之方法
TWI503323B (zh) *	2010-03-29	2015-10-11	Oncotherapy Science Inc	三環化合物以及含此化合物之ｐｂｋ抑制劑
EP2552923B1 (en)	2010-04-02	2014-03-26	Janssen R&D Ireland	Macrocyclic integrase inhibitors
JP5767393B2 (ja)	2011-03-31	2015-08-19	ファイザー・インク	新規二環式ピリジノン
CN104185420B (zh)	2011-11-30	2017-06-09	埃默里大学	用于治疗或预防逆转录病毒和其它病毒感染的抗病毒jak抑制剂
KR101365849B1 (ko) *	2012-03-28	2014-02-24	경동제약 주식회사	솔리페나신 또는 그의 염의 제조방법 및 이에 사용되는 신규 중간체
UA110688C2 (uk)	2012-09-21	2016-01-25	Пфайзер Інк.	Біциклічні піридинони
US10260089B2 (en)	2012-10-29	2019-04-16	The Research Foundation Of The State University Of New York	Compositions and methods for recognition of RNA using triple helical peptide nucleic acids
SG10202105371YA (en)	2014-12-26	2021-07-29	Univ Emory	N4-hydroxycytidine and derivatives and anti-viral uses related thereto
JP6628805B2 (ja)	2015-02-03	2020-01-15	ファイザー・インク	新規シクロプロパベンゾフラニルピリドピラジンジオン
CN104803905B (zh) *	2015-04-17	2017-10-10	复旦大学	一种合成异吲哚啉‑1‑酮衍生物的方法
CN107709288A (zh) *	2016-02-03	2018-02-16	四川海思科制药有限公司	一种磷酰胺衍生物及制备方法和用途
CN109305989B (zh) *	2017-07-28	2021-02-26	四川海思科制药有限公司	一种磷酰胺衍生物及制备方法和用途
CN109305990B (zh) *	2017-07-28	2021-02-26	四川海思科制药有限公司	一种磷酸衍生物及制备方法和用途
FI3706762T3 (fi)	2017-12-07	2024-12-13	Univ Emory	N4-hydroksisytidiini ja johdannaisia sekä niihin liittyviä virusten vastaisia käyttötapoja

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH385846A (de)	1960-03-31	1964-12-31	Geigy Ag J R	Verfahren zur Herstellung von neuen 7-Acyl-8-hydroxy-chinolinen und ihre Verwendung als Fungizide und Bakterizide im Pflanzen- und Materialschutz
US4816570A (en)	1982-11-30	1989-03-28	The Board Of Regents Of The University Of Texas System	Biologically reversible phosphate and phosphonate protective groups
US4968788A (en)	1986-04-04	1990-11-06	Board Of Regents, The University Of Texas System	Biologically reversible phosphate and phosphonate protective gruops
EP0533833B1 (en)	1990-06-13	1995-12-20	GLAZIER, Arnold	Phosphorous produgs
DE69129650T2 (de)	1990-09-14	1999-03-25	Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic, Prag/Praha	Wirkstoffvorläufer von Phosphonaten
JP3531944B2 (ja)	1991-02-07	2004-05-31	アベンティス・ファーマ・ソシエテ・アノニム	新規のベンジル基で置換された窒素系二環式誘導体及びその製造方法
EP0520573A1 (en)	1991-06-27	1992-12-30	Glaxo Inc.	Cyclic imide derivatives
US5639881A (en) *	1991-11-08	1997-06-17	Arizona Board Of Regents Acting On Behalf Of Arizona State University	Synthesis and elucidation of pyrimido (4,5-Q) quinazoline derivatives
TW304945B (is)	1992-06-27	1997-05-11	Hoechst Ag
US5798340A (en)	1993-09-17	1998-08-25	Gilead Sciences, Inc.	Nucleotide analogs
US5538988A (en)	1994-04-26	1996-07-23	Martinez; Gregory R.	Benzocycloalkylazolethione derivatives
US5854275A (en)	1996-05-16	1998-12-29	Pfizer Inc.	Cyclic imide derivatives
AU4172197A (en)	1996-09-10	1998-04-02	Pharmacia & Upjohn Company	8-hydroxy-7-substituted quinolines as anti-viral agents
WO1999007701A1 (en) *	1997-08-05	1999-02-18	Sugen, Inc.	Tricyclic quinoxaline derivatives as protein tyrosine kinase inhibitors
US6312662B1 (en)	1998-03-06	2001-11-06	Metabasis Therapeutics, Inc.	Prodrugs phosphorus-containing compounds
CA2329134A1 (en)	1998-06-03	1999-12-09	David L. Clark	Hiv integrase inhibitors
WO1999062520A1 (en)	1998-06-03	1999-12-09	Merck & Co., Inc.	Hiv integrase inhibitors
AU751590B2 (en) *	1998-06-10	2002-08-22	Arena Pharmaceuticals, Inc.	Acetylcholine enhancers
US6187907B1 (en)	1998-08-31	2001-02-13	James Chen	Triple helix coil template having a biologically active ligand
AU3118200A (en)	1998-12-14	2000-07-03	Merck & Co., Inc.	Hiv integrase inhibitors
ID29027A (id)	1998-12-25	2001-07-26	Shionogi & Co	Turunan-turunan heteroaromatik yang mempunyai aktivitas penghambatan terhadap integrase hiv
TR200103801T2 (tr)	1999-06-02	2002-04-22	Shonogi & Co., Ltd.	Yeni ikameli propenon türevlerinin hazırlanması için prosesler
AU5880600A (en)	1999-06-25	2001-01-31	Merck & Co., Inc.	1-(aromatic- or heteroaromatic-substituted)-3-(heteroaromatic substituted)-1,3-propanediones and uses thereof
US6245806B1 (en)	1999-08-03	2001-06-12	Merck & Co., Inc.	HIV integrase inhibitors
AU8009900A (en)	1999-10-13	2001-04-23	Merck & Co., Inc.	Hiv integrase inhibitors
WO2002030931A2 (en) *	2000-10-12	2002-04-18	Merck & Co., Inc.	Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors
CA2425625A1 (en)	2000-10-12	2002-07-18	Merck & Co., Inc.	Aza-and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors
CA2425067A1 (en)	2000-10-12	2002-05-10	Merck & Co., Inc.	Aza-and polyaza-naphthalenyl ketones useful as hiv integrase inhibitors
DE60128936T2 (de) *	2000-10-12	2008-04-10	Merck & Co, Inc.	Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer
WO2002030970A2 (en) *	2000-10-13	2002-04-18	Bayer Aktiengesellschaft	Human histone deacetylase gene
US6518767B1 (en) *	2000-10-19	2003-02-11	Schweitzer Engineering Laboratories, Inc.	Line differential protection system for a power transmission line
PL1742642T3 (pl) *	2004-04-14	2009-06-30	Gilead Sciences Inc	Analogi fosfonianowe związków inhibitorów integrazy HIV

2003
- 2003-10-15 AU AU2003301439A patent/AU2003301439A1/en not_active Abandoned
- 2003-10-15 US US10/687,374 patent/US20040157804A1/en not_active Abandoned
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- 2003-10-16 JP JP2005501423A patent/JP2006514099A/ja active Pending
- 2003-10-16 NZ NZ539264A patent/NZ539264A/en not_active IP Right Cessation
- 2003-10-16 EP EP03809030A patent/EP1558613A2/en not_active Withdrawn
- 2003-10-16 HR HR20050431A patent/HRP20050431A2/hr not_active Application Discontinuation
- 2003-10-16 EA EA200500660A patent/EA011399B1/ru not_active IP Right Cessation
- 2003-10-16 WO PCT/US2003/032666 patent/WO2004035576A2/en not_active Ceased
- 2003-10-16 CA CA002501881A patent/CA2501881A1/en not_active Abandoned
- 2003-10-16 MX MXPA05003950A patent/MXPA05003950A/es active IP Right Grant
- 2003-10-16 AU AU2003301306A patent/AU2003301306A1/en not_active Abandoned
- 2003-10-16 AP AP2005003279A patent/AP1858A/xx active
- 2003-10-16 OA OA1200500108A patent/OA13079A/en unknown
- 2003-10-16 UA UAA200504480A patent/UA79830C2/uk unknown
- 2003-10-16 KR KR1020057006668A patent/KR20050087787A/ko not_active Ceased
- 2003-10-16 CN CNB2003801061816A patent/CN100374438C/zh not_active Expired - Fee Related
- 2003-10-16 PL PL377966A patent/PL377966A1/pl not_active Application Discontinuation
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2005
- 2005-05-13 NO NO20052378A patent/NO20052378L/no not_active Application Discontinuation
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Publication number	Publication date
IS7845A (is)	2005-05-13
JP2006514099A (ja)	2006-04-27
HRP20050431A2 (en)	2005-10-31
US20040167124A1 (en)	2004-08-26
US20090029939A1 (en)	2009-01-29
WO2004035576A3 (en)	2004-06-24
NZ539264A (en)	2007-08-31
AP1858A (en)	2008-06-30
EA200500660A1 (ru)	2005-10-27
KR20050087787A (ko)	2005-08-31
MXPA05003950A (es)	2005-06-17
US7253180B2 (en)	2007-08-07
EA011399B1 (ru)	2009-02-27
AU2003301306A1 (en)	2004-05-04
PL377966A1 (pl)	2006-02-20
NO20052378D0 (no)	2005-05-13
UA79830C2 (en)	2007-07-25
BR0315405A (pt)	2005-08-09
CN1726212A (zh)	2006-01-25
CA2501881A1 (en)	2004-04-29
US20040157804A1 (en)	2004-08-12
AU2003301439A1 (en)	2004-05-04
AP2005003279A0 (en)	2005-06-30
WO2004035576A2 (en)	2004-04-29
EP1558613A2 (en)	2005-08-03
AU2003301439A8 (en)	2004-05-04
CN100374438C (zh)	2008-03-12
NO20052378L (no)	2005-07-18
WO2004035577A3 (en)	2004-07-29
WO2004035577A2 (en)	2004-04-29

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AU2005206511A1 (en)	2005-08-04	Pyrimidyl phosphonate antiviral compounds and methods of use
US20060217410A1 (en)	2006-09-28	Pre-organized tricyclic integrase inhibitor compounds
Androv et al.	2025	A new class of hybrid molecules based on azolo [1, 5-a] pyrimidin-7-ones and 3-ethoxycarbonyl-1-ethyl-6-fluoroquinolin-4 (1 H)-one linked by a 1, 2, 3-triazole spacer
US20080153783A1 (en)	2008-06-26	Pyrimidyl Phosphonate Antiviral Compounds and Methods of Use
Rose et al.	1999	Certain 3, 9-dideazapurines as inhibitors of purine nucleoside phosphorylase