TW450962B - Alpha-substituted pyrimidine-thioalkyl and alkylether compounds - Google Patents

Alpha-substituted pyrimidine-thioalkyl and alkylether compounds Download PDF

Info

Publication number: TW450962B
Authority: TW; Taiwan
Prior art keywords: dihydro; compound; pyridyl; amino; chloro
Prior art date: 1995-05-08

Application number

TW085105432A

Other languages

English (en)

Chinese (zh)

Inventor

Richard A Nugent

Stephen Thomas Schlachter

Michael J Murphy

Joel Morris

Richard C Thomas

Original Assignee

Pharmacia & Amp Upjohn 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.)

1995-05-08

Filing date

1996-05-07

Publication date

2001-08-21

1996-05-07 Application filed by Pharmacia & Amp Upjohn Company filed Critical Pharmacia & Amp Upjohn Company

2001-08-21 Application granted granted Critical

2001-08-21 Publication of TW450962B publication Critical patent/TW450962B/zh

Links

-1 alkylether compounds Chemical class 0.000 title claims abstract description 294
150000001875 compounds Chemical class 0.000 claims abstract description 352
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 435
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 327
125000004076 pyridyl group Chemical group 0.000 claims description 258
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 218
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 168
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 133
238000011049 filling Methods 0.000 claims description 125
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 123
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 123
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 118
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 117
238000006243 chemical reaction Methods 0.000 claims description 114
230000002079 cooperative effect Effects 0.000 claims description 92
LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 claims description 88
229910052717 sulfur Inorganic materials 0.000 claims description 88
239000011593 sulfur Substances 0.000 claims description 88
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 84
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 82
229910052757 nitrogen Inorganic materials 0.000 claims description 81
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 77
239000007789 gas Substances 0.000 claims description 69
239000007787 solid Substances 0.000 claims description 67
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims description 63
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 60
238000000034 method Methods 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 51
VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 33
125000001544 thienyl group Chemical group 0.000 claims description 29
239000000284 extract Substances 0.000 claims description 27
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 25
229920006395 saturated elastomer Polymers 0.000 claims description 24
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 22
125000004429 atom Chemical group 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 20
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 19
235000015170 shellfish Nutrition 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
239000012267 brine Substances 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
230000002441 reversible effect Effects 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
229910052938 sodium sulfate Inorganic materials 0.000 claims description 15
235000011152 sodium sulphate Nutrition 0.000 claims description 15
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 11
239000012141 concentrate Substances 0.000 claims description 11
238000007639 printing Methods 0.000 claims description 9
230000003612 virological effect Effects 0.000 claims description 9
238000009434 installation Methods 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000001041 indolyl group Chemical group 0.000 claims description 7
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
125000002347 octyl 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])[H] 0.000 claims description 7
238000010791 quenching Methods 0.000 claims description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
150000001335 aliphatic alkanes Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
208000011580 syndromic disease Diseases 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical compound OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
238000000605 extraction Methods 0.000 claims description 3
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
235000021286 stilbenes Nutrition 0.000 claims description 3
150000003573 thiols Chemical class 0.000 claims description 3
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
101100518501 Mus musculus Spp1 gene Proteins 0.000 claims description 2
241001674048 Phthiraptera Species 0.000 claims description 2
238000012937 correction Methods 0.000 claims description 2
RWIKCBHOVNDESJ-NSCUHMNNSA-N methyl (e)-4-bromobut-2-enoate Chemical compound COC(=O)\C=C\CBr RWIKCBHOVNDESJ-NSCUHMNNSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 6
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 1
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims 1
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
JPPBBGANXNRTBE-UHFFFAOYSA-N 3-chlorofuran Chemical compound ClC=1C=COC=1 JPPBBGANXNRTBE-UHFFFAOYSA-N 0.000 claims 1
OXGPFJHLALLRKU-UHFFFAOYSA-N 3-ethylfuro[2,3-c]pyridine Chemical compound N1=CC=C2C(CC)=COC2=C1 OXGPFJHLALLRKU-UHFFFAOYSA-N 0.000 claims 1
JYBWJPAOAQCXAX-UHFFFAOYSA-N 5-ethyl-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound CCC1=CNC(=S)NC1=O JYBWJPAOAQCXAX-UHFFFAOYSA-N 0.000 claims 1
101150041968 CDC13 gene Proteins 0.000 claims 1
102100034343 Integrase Human genes 0.000 claims 1
UIXLKBCZABYDGO-UHFFFAOYSA-N N1C=CC=2C=NC=CC21.C2=CC=C1C=CC3=CC=CC4=CC=C2C1=C34 Chemical compound N1C=CC=2C=NC=CC21.C2=CC=C1C=CC3=CC=CC4=CC=C2C1=C34 UIXLKBCZABYDGO-UHFFFAOYSA-N 0.000 claims 1
108010092799 RNA-directed DNA polymerase Proteins 0.000 claims 1
101100365036 Rattus norvegicus Scnn1a gene Proteins 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
UBKHHFOBCZFFKL-UHFFFAOYSA-N cyclopenta[c]pyran Chemical compound C1=COC=C2C=CC=C21 UBKHHFOBCZFFKL-UHFFFAOYSA-N 0.000 claims 1
230000007613 environmental effect Effects 0.000 claims 1
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
239000010931 gold Substances 0.000 claims 1
229910052737 gold Inorganic materials 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
125000001725 pyrenyl group Chemical group 0.000 claims 1
231100000241 scar Toxicity 0.000 claims 1
150000005215 alkyl ethers Chemical class 0.000 abstract description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 134
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 134
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 130
239000000243 solution Substances 0.000 description 117
239000000203 mixture Substances 0.000 description 115
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 108
239000012044 organic layer Substances 0.000 description 106
238000004809 thin layer chromatography Methods 0.000 description 103
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 100
235000019441 ethanol Nutrition 0.000 description 77
239000000741 silica gel Substances 0.000 description 75
229910002027 silica gel Inorganic materials 0.000 description 75
238000001819 mass spectrum Methods 0.000 description 73
230000008018 melting Effects 0.000 description 73
238000002844 melting Methods 0.000 description 73
239000003921 oil Substances 0.000 description 72
229910000027 potassium carbonate Inorganic materials 0.000 description 65
239000011541 reaction mixture Substances 0.000 description 55
238000004458 analytical method Methods 0.000 description 54
238000002329 infrared spectrum Methods 0.000 description 53
239000010410 layer Substances 0.000 description 52
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
239000013058 crude material Substances 0.000 description 47
239000002480 mineral oil Substances 0.000 description 46
235000010446 mineral oil Nutrition 0.000 description 46
238000005481 NMR spectroscopy Methods 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 44
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 41
239000012312 sodium hydride Substances 0.000 description 40
229910000104 sodium hydride Inorganic materials 0.000 description 40
238000010992 reflux Methods 0.000 description 39
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
238000002360 preparation method Methods 0.000 description 37
238000005160 1H NMR spectroscopy Methods 0.000 description 35
229920001296 polysiloxane Polymers 0.000 description 32
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 31
239000000706 filtrate Substances 0.000 description 29
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 27
238000003756 stirring Methods 0.000 description 27
238000004587 chromatography analysis Methods 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
230000002829 reductive effect Effects 0.000 description 22
208000030507 AIDS Diseases 0.000 description 20
102000004190 Enzymes Human genes 0.000 description 20
108090000790 Enzymes Proteins 0.000 description 20
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
235000019341 magnesium sulphate Nutrition 0.000 description 20
150000003385 sodium Chemical class 0.000 description 19
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 17
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 17
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
239000002585 base Substances 0.000 description 17
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 17
229940086542 triethylamine Drugs 0.000 description 17
229910052799 carbon Inorganic materials 0.000 description 16
239000011734 sodium Substances 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
239000004533 oil dispersion Substances 0.000 description 14
229910052708 sodium Inorganic materials 0.000 description 14
239000000725 suspension Substances 0.000 description 14
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
125000002541 furyl group Chemical group 0.000 description 13
239000007788 liquid Substances 0.000 description 13
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 12
238000010494 dissociation reaction Methods 0.000 description 12
230000005593 dissociations Effects 0.000 description 12
239000012065 filter cake Substances 0.000 description 12
239000000463 material Substances 0.000 description 12
239000003039 volatile agent Substances 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
239000000908 ammonium hydroxide Substances 0.000 description 11
238000001816 cooling Methods 0.000 description 11
239000006260 foam Substances 0.000 description 11
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
241000725303 Human immunodeficiency virus Species 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 10
239000000126 substance Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
BSKHPKMHTQYZBB-UHFFFAOYSA-N alpha-methylpyridine Natural products CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 9
150000001721 carbon Chemical group 0.000 description 9
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239000010948 rhodium Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
102200009479 rs141772938 Human genes 0.000 description 1
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239000012453 solvate Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000004079 stearyl 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])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
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BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
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125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
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230000002110 toxicologic effect Effects 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
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125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications

- 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
- C07D239/02—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
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/525—Isoalloxazines, e.g. riboflavins, vitamin B2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
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- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- 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
- C07D239/56—One oxygen atom and one sulfur atom
- 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
- C07D239/60—Three or more oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

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

TW085105432A 1995-05-08 1996-05-07 Alpha-substituted pyrimidine-thioalkyl and alkylether compounds TW450962B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US43670895A	1995-05-08	1995-05-08

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TW450962B true TW450962B (en)	2001-08-21

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TW085105432A TW450962B (en)	1995-05-08	1996-05-07	Alpha-substituted pyrimidine-thioalkyl and alkylether compounds

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US (1)	US6043248A (2)
EP (2)	EP0824524B1 (2)
JP (1)	JPH11507017A (2)
KR (1)	KR100445498B1 (2)
CN (2)	CN1535958A (2)
AT (1)	ATE275550T1 (2)
AU (1)	AU712404B2 (2)
BR (1)	BR9608265A (2)
CA (1)	CA2216099C (2)
CZ (1)	CZ293135B6 (2)
DE (1)	DE69633332T2 (2)
ES (1)	ES2227586T3 (2)
GE (1)	GEP20002297B (2)
HU (1)	HUP9801995A3 (2)
IL (1)	IL118075A0 (2)
MX (1)	MX9708582A (2)
NO (1)	NO310287B1 (2)
NZ (1)	NZ307089A (2)
PL (1)	PL323240A1 (2)
PT (1)	PT824524E (2)
RU (1)	RU2167155C2 (2)
SK (1)	SK150297A3 (2)
TW (1)	TW450962B (2)
UA (1)	UA56992C2 (2)
WO (1)	WO1996035678A1 (2)
ZA (1)	ZA963281B (2)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ503586A (en) *	1997-09-25	2002-03-28	Upjohn Co	Thioalkyl alpha substituted pyrimidine compounds for treating HIV.
US6111111A (en)	1997-10-23	2000-08-29	Kuraray Co., Ltd.	Intermediates for producing pyridine derivatives
US7358254B2 (en)	2001-07-13	2008-04-15	Bristol-Myers Squibb Company	Method for treating atherosclerosis employing an aP2 inhibitor and combination
GEP20033044B (en)	1998-09-17	2003-08-25	Bristol Myers Squibb Co	Method for Treating Atherosclerosis
JP2003503354A (ja)	1999-06-30	2003-01-28	メルクエンドカムパニーインコーポレーテッド	Ｓｒｃキナーゼ阻害剤化合物
AU5636900A (en)	1999-06-30	2001-01-31	Merck & Co., Inc.	Src kinase inhibitor compounds
WO2001000207A1 (en)	1999-06-30	2001-01-04	Merck & Co., Inc.	Src kinase inhibitor compounds
US7138404B2 (en) *	2001-05-23	2006-11-21	Hoffmann-La Roche Inc.	4-aminopyrimidine derivatives
MX2007006635A (es) *	2004-12-03	2007-06-19	Merck & Co Inc	Formulacion farmaceutica de inhibidores dela carboxamida vih integrasa que contienen una composicion que controla la velocidad de liberacion.
RU2401261C2 (ru) *	2005-03-04	2010-10-10	Тиботек Фармасьютикалз Лтд.	Ингибирующие вич 2-(4-цианофенил)-6-гидроксиламинопиримидины
US7923056B2 (en)	2007-06-01	2011-04-12	Illinois Tool Works Inc.	Method and apparatus for dispensing material on a substrate
US9040538B2 (en)	2009-05-21	2015-05-26	Universite Laval	Pyrimidines as novel therapeutic agents
CN101638391B (zh) *	2009-08-21	2011-04-27	山东大学	2-[(取代苯氨基)羰基甲硫基]-6-(2,6-二氯苄基)-3h-嘧啶-4-酮类衍生物及其制备方法与应用
US9226970B2 (en)	2010-02-22	2016-01-05	Nektar Therapeutics	Oligomer modified diaromatic substituted compounds
CA2793959C (en)	2010-03-25	2019-06-04	Oregon Health & Science University	Cmv glycoproteins and recombinant vectors
TWI453208B (zh) *	2010-07-02	2014-09-21	Gilead Sciences Inc	治療性化合物類
CA2832109C (en)	2011-06-10	2021-07-06	Oregon Health & Science University	Cmv glycoproteins and recombinant vectors
EP2568289A3 (en)	2011-09-12	2013-04-03	International AIDS Vaccine Initiative	Immunoselection of recombinant vesicular stomatitis virus expressing hiv-1 proteins by broadly neutralizing antibodies
US9402894B2 (en)	2011-10-27	2016-08-02	International Aids Vaccine Initiative	Viral particles derived from an enveloped virus
ES2631608T3 (es)	2012-06-27	2017-09-01	International Aids Vaccine Initiative	Variante de la glicoproteína Env del VIH-1
KR101360587B1 (ko) *	2012-11-01	2014-03-10	현대자동차주식회사	스마트 도어 언록 시스템
US20150065381A1 (en)	2013-09-05	2015-03-05	International Aids Vaccine Initiative	Methods of identifying novel hiv-1 immunogens
US10058604B2 (en)	2013-10-07	2018-08-28	International Aids Vaccine Initiative	Soluble HIV-1 envelope glycoprotein trimers
US10174292B2 (en)	2015-03-20	2019-01-08	International Aids Vaccine Initiative	Soluble HIV-1 envelope glycoprotein trimers
US9931394B2 (en)	2015-03-23	2018-04-03	International Aids Vaccine Initiative	Soluble HIV-1 envelope glycoprotein trimers
EP3324977B1 (en)	2015-07-22	2022-07-13	Enanta Pharmaceuticals, Inc.	Benzodiazepine derivatives as rsv inhibitors
GB201807898D0 (en) *	2018-05-15	2018-06-27	Kancera Ab	New processes and products with increased chiral purity
US11505558B1 (en)	2019-10-04	2022-11-22	Enanta Pharmaceuticals, Inc.	Antiviral heterocyclic compounds
WO2021066922A1 (en) *	2019-10-04	2021-04-08	Enanta Pharmaceuticals, Inc.	Antiviral heterocyclic compounds
WO2021149051A1 (en) *	2020-01-20	2021-07-29	Agrematch Ltd.	Compositions for crop protection
KR20240056718A (ko)	2021-08-10	2024-04-30	아이에프엠 듀, 인크.	Sting 활성과 연합된 상태를 치료하기 위한 화합물 및 조성물
CN114057707A (zh) *	2021-11-24	2022-02-18	上海应用技术大学	一种n-4-吲哚基-2-呋喃甲酰胺化合物的制备方法
JP2025504415A (ja) *	2022-01-12	2025-02-12	アイエフエムデューインコーポレイテッド	Ｓｔｉｎｇ活性に関連する病態を治療するための化合物及び組成物

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2295560A (en) *	1941-06-18	1942-09-15	Gen Electric	Pyrimidine derivatives
GB744867A (en) *	1952-10-29	1956-02-15	American Cyanamid Co	Improvements relating to 2-substituted-mercapto-4-amino-6-disubstituted-aminopyrimidines and acid addition salts thereof
US3940394A (en) *	1972-03-31	1976-02-24	Santilli Arthur A	2-pyrimidinylthio)alkanoic acids, esters, amides and hydrazides
US3940240A (en) *	1974-07-11	1976-02-24	Ina Seito Co., Ltd.	Baking method and kiln for tile
EP0124630B1 (de) *	1983-05-05	1987-01-28	LUDWIG HEUMANN & CO GMBH	Pyrimidin-Thioalkylpyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneimittel
US4724232A (en) *	1985-03-16	1988-02-09	Burroughs Wellcome Co.	Treatment of human viral infections
JPS62209062A (ja) *	1986-03-10	1987-09-14	Yamanouchi Pharmaceut Co Ltd	２−ピリジルメチルチオ−または２−ピリジルメチルスルフイニル−置換縮合環化合物
JPH07107056B2 (ja) *	1987-01-30	1995-11-15	日清製粉株式会社	４（３ｈ）−キナゾリノン誘導体、その製造方法およびそれを有効成分とする抗潰瘍剤
WO1989011279A1 (en) *	1988-05-16	1989-11-30	Georgia State University Foundation, Inc.	Nucleic acid interacting unfused heteropolycyclic compounds
HU203736B (en) *	1989-04-06	1991-09-30	Gyogyszerkutato Intezet	Process for producing new thiouracil-derivatives and pharmaceutical compositions containing them
MX9203454A (es) *	1989-12-28	1992-08-01	Upjohn Co	Compuestos anti sida diaromaticos substituidos.
US5668136A (en) *	1990-09-25	1997-09-16	Eisai Co., Ltd.	Trisubstituted benzene derivatives, composition and methods of treatment
EP0594702B1 (en) *	1991-07-03	1997-01-29	PHARMACIA & UPJOHN COMPANY	Substituted indoles as anti-aids pharmaceuticals
GB2266716A (en) *	1992-05-05	1993-11-10	Merck & Co Inc	Inhibitors of HIV reverse transcriptase
JP3077046B2 (ja) *	1992-08-31	2000-08-14	久光製薬株式会社	新規なキナゾリン誘導体
US5977169A (en) *	1993-09-17	1999-11-02	Chrusciel; Robert A.	Substituted tetronic acids useful for treating HIV and other retroviruses
US5981537A (en) *	1993-11-12	1999-11-09	Pharmacia & Upjohn Company	Pyrimidine-thioalkyl and alkylether compounds
US5945425A (en) *	1994-04-29	1999-08-31	G.D. Searle & Co.	Method of using (H+ /K+)ATPase inhibitors as antiviral agents
JPH10502660A (ja) *	1994-07-20	1998-03-10	ビイクグルデンロンベルクヒェーミッシェファブリークゲゼルシャフトミットベシュレンクテルハフツング	ヘリコバクター細菌に対抗するためのピリジルチオ化合物

1996
- 1996-03-05 UA UA97125800A patent/UA56992C2/uk unknown
- 1996-04-24 ZA ZA9603281A patent/ZA963281B/xx unknown
- 1996-04-29 IL IL11807596A patent/IL118075A0/xx unknown
- 1996-05-03 MX MX9708582A patent/MX9708582A/es not_active IP Right Cessation
- 1996-05-03 CZ CZ19973491A patent/CZ293135B6/cs not_active IP Right Cessation
- 1996-05-03 BR BR9608265A patent/BR9608265A/pt not_active Application Discontinuation
- 1996-05-03 GE GEAP19964013A patent/GEP20002297B/en unknown
- 1996-05-03 PL PL96323240A patent/PL323240A1/xx unknown
- 1996-05-03 ES ES96913306T patent/ES2227586T3/es not_active Expired - Lifetime
- 1996-05-03 WO PCT/US1996/006119 patent/WO1996035678A1/en not_active Ceased
- 1996-05-03 CA CA002216099A patent/CA2216099C/en not_active Expired - Fee Related
- 1996-05-03 AU AU56353/96A patent/AU712404B2/en not_active Ceased
- 1996-05-03 CN CNA200410032589XA patent/CN1535958A/zh active Pending
- 1996-05-03 PT PT96913306T patent/PT824524E/pt unknown
- 1996-05-03 AT AT96913306T patent/ATE275550T1/de not_active IP Right Cessation
- 1996-05-03 CN CNB961937912A patent/CN1152022C/zh not_active Expired - Fee Related
- 1996-05-03 NZ NZ307089A patent/NZ307089A/xx unknown
- 1996-05-03 SK SK1502-97A patent/SK150297A3/sk unknown
- 1996-05-03 EP EP96913306A patent/EP0824524B1/en not_active Expired - Lifetime
- 1996-05-03 JP JP8534120A patent/JPH11507017A/ja not_active Withdrawn
- 1996-05-03 KR KR1019970707927A patent/KR100445498B1/ko not_active Expired - Fee Related
- 1996-05-03 US US08/945,153 patent/US6043248A/en not_active Expired - Fee Related
- 1996-05-03 RU RU97120116/04A patent/RU2167155C2/ru not_active IP Right Cessation
- 1996-05-03 EP EP04010159A patent/EP1449835A3/en not_active Withdrawn
- 1996-05-03 HU HU9801995A patent/HUP9801995A3/hu unknown
- 1996-05-03 DE DE69633332T patent/DE69633332T2/de not_active Expired - Fee Related
- 1996-05-07 TW TW085105432A patent/TW450962B/zh not_active IP Right Cessation
1997
- 1997-11-07 NO NO19975129A patent/NO310287B1/no unknown

Also Published As

Publication number	Publication date
RU2167155C2 (ru)	2001-05-20
CZ293135B6 (cs)	2004-02-18
HUP9801995A2 (hu)	1999-03-29
ES2227586T3 (es)	2005-04-01
EP0824524A1 (en)	1998-02-25
EP1449835A3 (en)	2004-09-15
DE69633332T2 (de)	2005-09-22
WO1996035678A1 (en)	1996-11-14
CZ349197A3 (cs)	1998-04-15
HK1009446A1 (en)	1999-09-10
BR9608265A (pt)	1999-02-02
MX9708582A (es)	1998-02-28
PL323240A1 (en)	1998-03-16
AU712404B2 (en)	1999-11-04
CN1183773A (zh)	1998-06-03
KR100445498B1 (ko)	2004-11-16
PT824524E (pt)	2005-01-31
HUP9801995A3 (en)	1999-04-28
EP1449835A2 (en)	2004-08-25
AU5635396A (en)	1996-11-29
EP0824524B1 (en)	2004-09-08
CN1535958A (zh)	2004-10-13
GEP20002297B (en)	2000-11-25
UA56992C2 (uk)	2003-06-16
CA2216099A1 (en)	1996-11-14
CN1152022C (zh)	2004-06-02
NO975129D0 (no)	1997-11-07
US6043248A (en)	2000-03-28
CA2216099C (en)	2005-09-13
ZA963281B (en)	1997-10-24
NZ307089A (en)	1999-07-29
ATE275550T1 (de)	2004-09-15
DE69633332D1 (de)	2004-10-14
SK150297A3 (en)	1998-10-07
IL118075A0 (en)	1996-08-04
NO975129L (no)	1998-01-07
JPH11507017A (ja)	1999-06-22
KR19990008400A (ko)	1999-01-25
NO310287B1 (no)	2001-06-18

Legal Events

Date	Code	Title	Description
2001-12-07	GD4A	Issue of patent certificate for granted invention patent
2006-06-21	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
TW450962B (en)	2001-08-21	Alpha-substituted pyrimidine-thioalkyl and alkylether compounds
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US8637549B2 (en)	2014-01-28	Pyridons as PDK1 inhibitors
AU2013339167B2 (en)	2018-03-15	Novel amine derivative or salt thereof
TW201014859A (en)	2010-04-16	New compounds for the treatment of CNS disorders
PT1042293E (pt)	2008-04-18	Compostos de piridazina e piridina substituídos e as suas utilizações farmacêuticas
UA125874C2 (uk)	2022-06-29	Позитивні алостеричні модулятори мускаринового ацетилхолінового рецептора м4
KR20170117479A (ko)	2017-10-23	치환된 모노- 및 폴리아자나프탈렌 유도체 및 이의 용도
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JP2006520795A (ja)	2006-09-14	カンナビノイドレセプターリガンド
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US20070004684A1 (en)	2007-01-04	Alpha-Carbolines as CDK-1 inhibitors
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WO2017108203A1 (en)	2017-06-29	Novel substituted indoline compounds as phosphodiesterase inhibitors
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USRE47493E1 (en)	2019-07-09	Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity