SK287900B6 - Substituted azaindolexoacetic piperazine derivatives and pharmaceutical composition containing thereof - Google Patents

Substituted azaindolexoacetic piperazine derivatives and pharmaceutical composition containing thereof Download PDF

Info

Publication number: SK287900B6
Authority: SK; Slovakia
Prior art keywords: alkyl; group; heteroaryl; cycloalkyl; heteroalicyclic
Prior art date: 2001-02-02

Application number

SK959-2003A

Other languages

English (en)

Slovak (sk)

Other versions

SK9592003A3 (en

Inventor

Tao Wang

Zhongxing Zhang

Nicholas A. Meanwell

John F. Kadow

Zhiwei Yin

Original Assignee

Bristol-Myers Squibb Company

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.)

2001-02-02

Filing date

2002-01-02

Publication date

2012-03-02

2002-01-02 Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company

2004-08-03 Publication of SK9592003A3 publication Critical patent/SK9592003A3/sk

2012-03-02 Publication of SK287900B6 publication Critical patent/SK287900B6/sk

Links

150000004885 piperazines Chemical class 0.000 title abstract description 20
239000008194 pharmaceutical composition Substances 0.000 title abstract description 7
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 261
125000000217 alkyl group Chemical group 0.000 claims description 248
150000001875 compounds Chemical class 0.000 claims description 176
125000000753 cycloalkyl group Chemical group 0.000 claims description 172
229910052736 halogen Inorganic materials 0.000 claims description 170
125000003118 aryl group Chemical group 0.000 claims description 165
-1 benzoimidazolyl Chemical group 0.000 claims description 164
150000002367 halogens Chemical class 0.000 claims description 162
125000001424 substituent group Chemical group 0.000 claims description 133
229910052739 hydrogen Inorganic materials 0.000 claims description 114
239000001257 hydrogen Substances 0.000 claims description 99
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 85
229910052731 fluorine Inorganic materials 0.000 claims description 66
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
229910052757 nitrogen Inorganic materials 0.000 claims description 63
125000000304 alkynyl group Chemical group 0.000 claims description 60
125000003545 alkoxy group Chemical group 0.000 claims description 55
239000000460 chlorine Substances 0.000 claims description 50
125000000392 cycloalkenyl group Chemical group 0.000 claims description 50
125000003342 alkenyl group Chemical group 0.000 claims description 45
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 44
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 44
125000004093 cyano group Chemical group *C#N 0.000 claims description 42
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 42
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
229910052760 oxygen Inorganic materials 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
229910052717 sulfur Inorganic materials 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 34
125000004122 cyclic group Chemical group 0.000 claims description 32
125000001544 thienyl group Chemical group 0.000 claims description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 29
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
125000005842 heteroatom Chemical group 0.000 claims description 23
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000002541 furyl group Chemical group 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 22
229910052796 boron Inorganic materials 0.000 claims description 21
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000005309 thioalkoxy group Chemical group 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000005296 thioaryloxy group Chemical group 0.000 claims description 18
125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 16
150000003536 tetrazoles Chemical class 0.000 claims description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
125000005404 thioheteroaryloxy group Chemical group 0.000 claims description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 14
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 14
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
125000005190 thiohydroxy group Chemical group 0.000 claims description 14
150000003852 triazoles Chemical class 0.000 claims description 14
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 13
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 13
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 13
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 13
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 13
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 13
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 10
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 9
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
125000001786 isothiazolyl group Chemical group 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
125000005499 phosphonyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000004306 triazinyl group Chemical group 0.000 claims description 5
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000005956 isoquinolyl group Chemical group 0.000 claims description 3
125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000005493 quinolyl group Chemical group 0.000 claims description 3
125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000005872 benzooxazolyl group Chemical group 0.000 claims 1
150000003950 cyclic amides Chemical class 0.000 claims 1
108010011222 cyclo(Arg-Pro) Proteins 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
229940124530 sulfonamide Drugs 0.000 claims 1
150000003456 sulfonamides Chemical class 0.000 claims 1
208000030507 AIDS Diseases 0.000 abstract description 78
238000011282 treatment Methods 0.000 abstract description 20
239000000543 intermediate Substances 0.000 description 313
238000000034 method Methods 0.000 description 170
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 124
238000006243 chemical reaction Methods 0.000 description 117
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
238000004949 mass spectrometry Methods 0.000 description 64
239000002904 solvent Substances 0.000 description 64
239000000203 mixture Substances 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
238000004128 high performance liquid chromatography Methods 0.000 description 54
238000002360 preparation method Methods 0.000 description 52
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 51
230000015572 biosynthetic process Effects 0.000 description 50
230000014759 maintenance of location Effects 0.000 description 47
239000011541 reaction mixture Substances 0.000 description 45
239000000243 solution Substances 0.000 description 45
208000031886 HIV Infections Diseases 0.000 description 44
208000037357 HIV infectious disease Diseases 0.000 description 42
239000002253 acid Substances 0.000 description 42
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 42
238000003786 synthesis reaction Methods 0.000 description 40
125000000623 heterocyclic group Chemical group 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
239000002585 base Substances 0.000 description 35
235000019439 ethyl acetate Nutrition 0.000 description 35
239000003153 chemical reaction reagent Substances 0.000 description 34
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
150000001299 aldehydes Chemical class 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 27
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 24
150000001412 amines Chemical class 0.000 description 24
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 24
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
238000009833 condensation Methods 0.000 description 22
230000005494 condensation Effects 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
229910000104 sodium hydride Inorganic materials 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
238000005481 NMR spectroscopy Methods 0.000 description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000003814 drug Substances 0.000 description 21
238000004811 liquid chromatography Methods 0.000 description 21
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 21
241000725303 Human immunodeficiency virus Species 0.000 description 20
229960002555 zidovudine Drugs 0.000 description 20
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 19
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
230000009466 transformation Effects 0.000 description 19
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 17
238000010898 silica gel chromatography Methods 0.000 description 17
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 16
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 16
AJDPNPAGZMZOMN-UHFFFAOYSA-N diethyl (4-oxo-1,2,3-benzotriazin-3-yl) phosphate Chemical compound C1=CC=C2C(=O)N(OP(=O)(OCC)OCC)N=NC2=C1 AJDPNPAGZMZOMN-UHFFFAOYSA-N 0.000 description 16
239000012044 organic layer Substances 0.000 description 16
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
150000001204 N-oxides Chemical class 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
150000001408 amides Chemical class 0.000 description 15
244000309464 bull Species 0.000 description 15
229910052801 chlorine Inorganic materials 0.000 description 15
150000002825 nitriles Chemical class 0.000 description 15
239000007787 solid Substances 0.000 description 15
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
229910052794 bromium Inorganic materials 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
125000003277 amino group Chemical group 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000000284 extract Substances 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 12
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
230000007062 hydrolysis Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
239000000137 peptide hydrolase inhibitor Substances 0.000 description 11
238000010791 quenching Methods 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
208000007766 Kaposi sarcoma Diseases 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
239000003112 inhibitor Substances 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
229910052744 lithium Inorganic materials 0.000 description 10
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000007858 starting material Substances 0.000 description 10
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
229910021589 Copper(I) bromide Inorganic materials 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 9
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 9
235000019270 ammonium chloride Nutrition 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 9
238000001816 cooling Methods 0.000 description 9
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 9
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 9
229960001936 indinavir Drugs 0.000 description 9
150000002475 indoles Chemical class 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
230000008569 process Effects 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000000844 transformation Methods 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
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
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ATEBXHFBFRCZMA-VXTBVIBXSA-N rifabutin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC(=C2N3)C(=O)C=4C(O)=C5C)C)OC)C5=C1C=4C2=NC13CCN(CC(C)C)CC1 ATEBXHFBFRCZMA-VXTBVIBXSA-N 0.000 description 1
229960000885 rifabutin Drugs 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
JWHQWQQROAZMII-UHFFFAOYSA-N semicochliodinol B Chemical compound C1=CC=C2C(C=3C(=O)C(O)=C(C(C=3O)=O)C=3C4=CC=C(C=C4NC=3)CC=C(C)C)=CNC2=C1 JWHQWQQROAZMII-UHFFFAOYSA-N 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000019372 spiramycin Nutrition 0.000 description 1
229960001294 spiramycin Drugs 0.000 description 1
229930191512 spiramycin Natural products 0.000 description 1
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
229910000080 stannane Inorganic materials 0.000 description 1
229940071182 stannate Drugs 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003883 substance clean up Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
150000003549 thiazolines Chemical class 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
229960004517 thymopentin Drugs 0.000 description 1
SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 description 1
229960000838 tipranavir Drugs 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
125000004385 trihaloalkyl group Chemical group 0.000 description 1
NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
229960001099 trimetrexate Drugs 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
229940093257 valacyclovir Drugs 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
229940100050 virazole Drugs 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Virology (AREA)
Engineering & Computer Science (AREA)
AIDS & HIV (AREA)
Molecular Biology (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SK959-2003A 2001-02-02 2002-01-02 Substituted azaindolexoacetic piperazine derivatives and pharmaceutical composition containing thereof SK287900B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US26618301P	2001-02-02	2001-02-02
US31440601P	2001-08-23	2001-08-23
PCT/US2002/000455 WO2002062423A1 (en)	2001-02-02	2002-01-02	Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives

Publications (2)

Publication Number	Publication Date
SK9592003A3 SK9592003A3 (en)	2004-08-03
SK287900B6 true SK287900B6 (sk)	2012-03-02

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US (1)	US20030069266A1 (is)
EP (1)	EP1363705B9 (is)
JP (1)	JP4328527B2 (is)
KR (1)	KR20030079979A (is)
CN (1)	CN100384423C (is)
AR (1)	AR034292A1 (is)
BG (1)	BG66359B1 (is)
BR (1)	BRPI0206636B8 (is)
CA (1)	CA2437524C (is)
CY (1)	CY1113194T1 (is)
CZ (1)	CZ303750B6 (is)
DK (1)	DK1363705T3 (is)
EE (1)	EE05424B1 (is)
ES (1)	ES2387981T3 (is)
HK (1)	HK1056698A1 (is)
HR (1)	HRP20030694A2 (is)
HU (1)	HU229305B1 (is)
IL (2)	IL157029A0 (is)
IS (1)	IS2912B (is)
MX (1)	MXPA03006939A (is)
MY (1)	MY137480A (is)
NO (1)	NO326510B1 (is)
NZ (1)	NZ527193A (is)
PE (1)	PE20020855A1 (is)
PL (1)	PL364279A1 (is)
PT (1)	PT1363705E (is)
RS (1)	RS52489B (is)
RU (1)	RU2303038C2 (is)
SK (1)	SK287900B6 (is)
TW (1)	TWI318978B (is)
WO (1)	WO2002062423A1 (is)
ZA (1)	ZA200305885B (is)

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2002
- 2002-01-02 US US10/038,306 patent/US20030069266A1/en not_active Abandoned
- 2002-01-02 MX MXPA03006939A patent/MXPA03006939A/es active IP Right Grant
- 2002-01-02 RS YU60903A patent/RS52489B/en unknown
- 2002-01-02 NZ NZ527193A patent/NZ527193A/en not_active IP Right Cessation
- 2002-01-02 EP EP02707413A patent/EP1363705B9/en not_active Expired - Lifetime
- 2002-01-02 PT PT02707413T patent/PT1363705E/pt unknown
- 2002-01-02 CN CNB028078268A patent/CN100384423C/zh not_active Expired - Lifetime
- 2002-01-02 WO PCT/US2002/000455 patent/WO2002062423A1/en active IP Right Grant
- 2002-01-02 EE EEP200300359A patent/EE05424B1/xx unknown
- 2002-01-02 ES ES02707413T patent/ES2387981T3/es not_active Expired - Lifetime
- 2002-01-02 JP JP2002562428A patent/JP4328527B2/ja not_active Expired - Lifetime
- 2002-01-02 BR BR0206636-0 patent/BRPI0206636B8/pt not_active IP Right Cessation
- 2002-01-02 CA CA2437524A patent/CA2437524C/en not_active Expired - Lifetime
- 2002-01-02 KR KR10-2003-7010208A patent/KR20030079979A/ko not_active Application Discontinuation
- 2002-01-02 SK SK959-2003A patent/SK287900B6/sk not_active IP Right Cessation
- 2002-01-02 HU HU0304062A patent/HU229305B1/hu unknown
- 2002-01-02 IL IL15702902A patent/IL157029A0/xx unknown
- 2002-01-02 DK DK02707413.7T patent/DK1363705T3/da active
- 2002-01-02 RU RU2003127077/04A patent/RU2303038C2/ru active
- 2002-01-02 PL PL02364279A patent/PL364279A1/xx unknown
- 2002-01-02 CZ CZ20032316A patent/CZ303750B6/cs not_active IP Right Cessation
- 2002-01-18 MY MYPI20020202A patent/MY137480A/en unknown
- 2002-01-23 TW TW091101013A patent/TWI318978B/zh not_active IP Right Cessation
- 2002-01-31 AR ARP020100336A patent/AR034292A1/es active IP Right Grant
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2003
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- 2003-07-30 ZA ZA2003/05885A patent/ZA200305885B/en unknown
- 2003-07-30 IS IS6899A patent/IS2912B/is unknown
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Also Published As

Publication number	Publication date
IS6899A (is)	2003-07-30
ZA200305885B (en)	2005-01-26
EP1363705A1 (en)	2003-11-26
PL364279A1 (en)	2004-12-13
RU2003127077A (ru)	2005-03-20
AR034292A1 (es)	2004-02-18
WO2002062423A1 (en)	2002-08-15
EP1363705B1 (en)	2012-06-13
BRPI0206636B8 (pt)	2021-05-25
HRP20030694A2 (en)	2005-04-30
KR20030079979A (ko)	2003-10-10
ES2387981T3 (es)	2012-10-05
NO20033436L (no)	2003-10-01
TWI318978B (en)	2010-01-01
HU229305B1 (en)	2013-10-28
MY137480A (en)	2009-01-30
JP4328527B2 (ja)	2009-09-09
US20030069266A1 (en)	2003-04-10
NO326510B1 (no)	2008-12-22
EP1363705B9 (en)	2012-11-07
IL157029A (en)	2015-11-30
HK1056698A1 (en)	2004-02-27
EP1363705A4 (en)	2009-08-12
CZ303750B6 (cs)	2013-04-17
YU60903A (sh)	2006-05-25
HUP0304062A3 (en)	2010-06-28
MXPA03006939A (es)	2003-11-18
EE05424B1 (et)	2011-06-15
SK9592003A3 (en)	2004-08-03
CZ20032316A3 (cs)	2004-01-14
CY1113194T1 (el)	2016-04-13
CA2437524C (en)	2010-04-27
EE200300359A (et)	2003-12-15
PE20020855A1 (es)	2002-09-27
DK1363705T3 (da)	2012-09-24
RS52489B (en)	2013-02-28
IS2912B (is)	2014-11-15
CN1612763A (zh)	2005-05-04
BG66359B1 (bg)	2013-09-30
JP2004522755A (ja)	2004-07-29
RU2303038C2 (ru)	2007-07-20
BG108021A (bg)	2004-04-30
CA2437524A1 (en)	2002-08-15
IL157029A0 (en)	2004-02-08
BRPI0206636B1 (pt)	2018-05-02
CN100384423C (zh)	2008-04-30
NZ527193A (en)	2004-05-28
PT1363705E (pt)	2012-08-17
NO20033436D0 (no)	2003-08-01
BR0206636A (pt)	2004-02-25
HUP0304062A2 (hu)	2004-04-28

Legal Events

Date

Code

Title

Description

2017-10-03

PC4A

Assignment and transfer of rights

Owner name: VIIV HEALTHCARE UK (NO.4) LIMITED, BRENTFORD, , GB

Free format text: FORMER OWNER: BRISTOL-MYERS SQUIBB COMPANY, PRINCETON, NJ, US

Effective date: 20170913

2022-02-23

MK4A

Expiry of patent

Expiry date: 20220102