IL95956A - Vaccines used to stop the growth and folding of VIH - Google Patents
Vaccines used to stop the growth and folding of VIHInfo
- Publication number
- IL95956A IL95956A IL9595690A IL9595690A IL95956A IL 95956 A IL95956 A IL 95956A IL 9595690 A IL9595690 A IL 9595690A IL 9595690 A IL9595690 A IL 9595690A IL 95956 A IL95956 A IL 95956A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- amino
- chloro
- hydrogen
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 170
- 230000012010 growth Effects 0.000 title claims abstract description 13
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 11
- 230000010076 replication Effects 0.000 title claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 163
- 229910052739 hydrogen Inorganic materials 0.000 claims description 105
- 239000001257 hydrogen Substances 0.000 claims description 104
- -1 trifluoromethoxy, methylthio, nitro, cyano, acetoxy Chemical group 0.000 claims description 96
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 94
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 85
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 83
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 150000002431 hydrogen Chemical group 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 230000002829 reductive effect Effects 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 20
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 125000004193 piperazinyl group Chemical group 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 235000000346 sugar Nutrition 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 229910052701 rubidium Inorganic materials 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004416 alkarylalkyl group Chemical group 0.000 claims description 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 125000003566 oxetanyl group Chemical group 0.000 claims description 9
- 125000000466 oxiranyl group Chemical group 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 125000000597 dioxinyl group Chemical group 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000005333 aroyloxy group Chemical group 0.000 claims description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006544 oxetanylalkyl group Chemical group 0.000 claims description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
- XXZDYDXEASTJNF-UHFFFAOYSA-N propan-2-yl 5-benzamido-2-chlorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(NC(=O)C=2C=CC=CC=2)=C1 XXZDYDXEASTJNF-UHFFFAOYSA-N 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- JSDYXQZCCWYDBR-UHFFFAOYSA-N propan-2-yl 5-[(2-bromobenzoyl)amino]-2-chlorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(NC(=O)C=2C(=CC=CC=2)Br)=C1 JSDYXQZCCWYDBR-UHFFFAOYSA-N 0.000 claims description 2
- XZZXDZXDQPFXIW-UHFFFAOYSA-N propan-2-yl 5-benzamido-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(NC(=O)C=2C=CC=CC=2)=C1F XZZXDZXDQPFXIW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- PLUZLNLFFQNOMD-UHFFFAOYSA-N propyl 2-chloro-5-[(6-methyl-2,3-dihydro-1,4-oxathiine-5-carbonyl)amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OCCC)=CC(NC(=O)C=2SCCOC=2C)=C1 PLUZLNLFFQNOMD-UHFFFAOYSA-N 0.000 claims 2
- AXTNFJKQZPETJA-UHFFFAOYSA-N 1-methyl ethyl 2-chloro-5-[[[(1-methylethoxy)thiooxo]methyl]amino]-benzoate Chemical compound CC(C)OC(=S)NC1=CC=C(Cl)C(C(=O)OC(C)C)=C1 AXTNFJKQZPETJA-UHFFFAOYSA-N 0.000 claims 1
- 125000002379 2-iodobenzoyl group Chemical group IC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 1
- DXRFHOBQCQPXGT-UHFFFAOYSA-N ethyl 2-chloro-5-[(2-methoxybenzoyl)amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(NC(=O)C=2C(=CC=CC=2)OC)=C1 DXRFHOBQCQPXGT-UHFFFAOYSA-N 0.000 claims 1
- YFRQVBZHCWKGRO-UHFFFAOYSA-N ethyl 5-[(2-aminobenzoyl)amino]-2-chlorobenzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(NC(=O)C=2C(=CC=CC=2)N)=C1 YFRQVBZHCWKGRO-UHFFFAOYSA-N 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
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- CKPVYAKZEQOQNK-UHFFFAOYSA-N propan-2-yl 5-(butoxycarbonylamino)-2-chlorobenzoate Chemical compound CCCCOC(=O)NC1=CC=C(Cl)C(C(=O)OC(C)C)=C1 CKPVYAKZEQOQNK-UHFFFAOYSA-N 0.000 claims 1
- LOTPCTPCZAGFIT-UHFFFAOYSA-N propyl 2-chloro-5-[(2-methylbenzoyl)amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OCCC)=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 LOTPCTPCZAGFIT-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 abstract description 31
- 238000000034 method Methods 0.000 abstract description 21
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 206
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 104
- 239000000243 solution Substances 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- 210000004027 cell Anatomy 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 44
- 229940050390 benzoate Drugs 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 230000000694 effects Effects 0.000 description 36
- 238000012360 testing method Methods 0.000 description 36
- 239000003921 oil Substances 0.000 description 32
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- 239000007787 solid Substances 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- 101150041968 CDC13 gene Proteins 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- 241000725303 Human immunodeficiency virus Species 0.000 description 26
- 239000002904 solvent Substances 0.000 description 22
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- 238000005406 washing Methods 0.000 description 17
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
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- 238000003756 stirring Methods 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 102000053602 DNA Human genes 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 230000036436 anti-hiv Effects 0.000 description 11
- XEHDGJHIPJRFLH-UHFFFAOYSA-N propan-2-yl 5-amino-2-chlorobenzoate Chemical compound CC(C)OC(=O)C1=CC(N)=CC=C1Cl XEHDGJHIPJRFLH-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 108020004414 DNA Proteins 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 101150060670 MT2C gene Proteins 0.000 description 10
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- 238000002360 preparation method Methods 0.000 description 10
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 230000000120 cytopathologic effect Effects 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
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- YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical class O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
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- 231100000419 toxicity Toxicity 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 208000031886 HIV Infections Diseases 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
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- C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
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- C07C327/00—Thiocarboxylic acids
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- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with 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
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2475—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aralkylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US42115589A | 1989-10-16 | 1989-10-16 | |
US56798290A | 1990-08-15 | 1990-08-15 | |
US07/588,208 US5268389A (en) | 1989-10-16 | 1990-09-26 | Thiocarboxylate ester compounds compositions containing the same |
Publications (2)
Publication Number | Publication Date |
---|---|
IL95956A0 IL95956A0 (en) | 1991-07-18 |
IL95956A true IL95956A (en) | 1996-03-31 |
Family
ID=27411301
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL9595690A IL95956A (en) | 1989-10-16 | 1990-10-10 | Vaccines used to stop the growth and folding of VIH |
Country Status (16)
Country | Link |
---|---|
US (2) | US5268389A (de) |
EP (1) | EP0497816B1 (de) |
JP (1) | JPH06102641B2 (de) |
KR (1) | KR100222233B1 (de) |
CN (1) | CN1051036A (de) |
AT (1) | ATE122654T1 (de) |
AU (1) | AU636409B2 (de) |
BR (1) | BR9007758A (de) |
CA (1) | CA2067381C (de) |
DE (1) | DE69019533T2 (de) |
DK (1) | DK0497816T3 (de) |
GR (1) | GR3017128T3 (de) |
HU (1) | HU220759B1 (de) |
IL (1) | IL95956A (de) |
RU (1) | RU2108785C1 (de) |
WO (1) | WO1991005761A1 (de) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
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US5146321A (en) * | 1991-06-12 | 1992-09-08 | Eastman Kodak Company | Linear film scanner operable at different line rates |
US5527819A (en) * | 1991-09-06 | 1996-06-18 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
WO1993005020A1 (en) * | 1991-09-06 | 1993-03-18 | Merck & Co., Inc. | Indoles as inhibitors of hiv reverse transcriptase |
BR9405737A (pt) * | 1993-02-24 | 1995-12-05 | Merck & Co Inc | Composto processo de inibição de transcriptase reserva de HIV, processo de prevenção contra a infecção pelo HIV ou de tratamento da infecção pelo HIV, composição farmacêutica útil para a inibição da transcriptase reserva de HIV, e, útil para a prevenção ou tratamento de infecção pelo HIV ou para o tratamento da AIDS ou ARC |
US5968910A (en) * | 1994-11-30 | 1999-10-19 | Jan M. R. Balzarini | Compositions containing two or three inhibitors of different HIV reverse transcriptases |
US5550280A (en) * | 1994-11-30 | 1996-08-27 | Uniroyal Chemical Ltd./ Uniroyal Chemical Ltee | Hindered aromatic ester compounds useful as anti-viral agents |
US5663199A (en) * | 1994-11-30 | 1997-09-02 | Uniroyal Chemical Ltd./Ltee | Anti-viral aromatic O-alkylated oximes, ethers and thioethers |
US5580544A (en) * | 1995-03-29 | 1996-12-03 | Uniroyal Chemical Company, Inc. | Paste formulation useful for seed treatment and foliar treatment of plants |
US5696151A (en) * | 1995-11-30 | 1997-12-09 | Uniroyal Chemical Company, Inc. | Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants |
US6498265B2 (en) | 1995-12-21 | 2002-12-24 | Syngenta Investment Corporation | 3-amino-2-mercaptobenzoic acid derivatives and processes for their preparation |
US5847147A (en) * | 1996-12-20 | 1998-12-08 | Novartis Corp. | 3-Amino-2-mercaptobenzoic acid derivatives and processes for their preparation |
US5914351A (en) * | 1997-12-12 | 1999-06-22 | Uniroyal Chemical Company, Inc. | Anti-viral aromatic hydrazones |
BR9911385A (pt) * | 1998-06-19 | 2001-03-13 | Us Health | Composição, processos para dissociar um ìon de metal de uma proteìna contendo dedo de zinco, para inativar um vìrus e para selecionar um composto capaz de dissociar um ìon de metal quelado com um dedo de zinco de uma proteìna viral, vìrus isolado e inativado, kit para selecionar um composto capaz de dissociar um ìon de metal de um dedo de zinco de uma proteìna viral, composição viricida, e, formulação farmacêutica. |
MXPA01009397A (es) * | 1999-03-25 | 2002-06-04 | Boehringer Ingelheim Ltd | Inhibidores de primasa de virus de herpes simplex. |
AU2001277731A1 (en) | 2000-08-09 | 2002-02-18 | Welfide Corporation | Fused bicyclic amide compounds and medicinal use thereof |
MXPA04001253A (es) * | 2001-08-09 | 2004-06-03 | Ono Pharmaceutical Co | Derivados de acidos carboxilicos y agente farmaceutico que comprende los mismos como ingrediente activo. |
US6498254B1 (en) * | 2001-10-29 | 2002-12-24 | Uniroyal Chemical Company, Inc. | Antiretroviral compounds and compositions |
US7064139B2 (en) * | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
MX263097B (es) | 2002-03-11 | 2008-12-15 | Tibotec Pharm Ltd | Inhibidores de entrada a moleculas pequenas. |
CA2506415A1 (en) | 2002-11-19 | 2004-06-03 | Achillion Pharmaceuticals, Inc. | Substituted aryl thioureas and releated compounds; inhibitors of viral replication |
WO2007052843A1 (ja) * | 2005-11-04 | 2007-05-10 | Takeda Pharmaceutical Company Limited | 複素環アミド化合物およびその用途 |
EP2506841A1 (de) * | 2009-12-01 | 2012-10-10 | Seprox Biotech, S.L. | Topische verwendung von hydroxytyrosol und derivaten für die prävention von hiv-infektion |
CN113754613B (zh) * | 2021-09-27 | 2023-06-30 | 北京工商大学 | 一种4-烯醇的苯硫基环醚化方法 |
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US3249499A (en) | 1965-04-26 | 1966-05-03 | Us Rubber Co | Control of plant diseases |
NL134133C (de) | 1965-11-05 | |||
US3454391A (en) | 1966-05-04 | 1969-07-08 | Uniroyal Inc | Stimulation of plant growth |
US3657449A (en) | 1970-03-09 | 1972-04-18 | Uniroyal Inc | Control of virus diseases of plants with carboxamido oxathins |
US3806332A (en) | 1970-03-09 | 1974-04-23 | Uniroyal Ltd | Plant air pollution protectants |
FR2143577A1 (en) * | 1971-06-30 | 1973-02-09 | Ugine Kuhlmann | 3-(2-chlorobenzamido)benzoic acids and salts - with uricosuric activity |
IL46853A0 (en) * | 1974-03-20 | 1975-05-22 | Bayer Ag | Novel alkoxycarbonylphenylureas,their preparation and their use as herbicides |
US4004018A (en) | 1974-06-20 | 1977-01-18 | Uniroyal Inc. | 2,3-Dihydro-1,4-dithiin 1,1,4,4-tetroxide antimicrobials |
US4197124A (en) * | 1975-07-29 | 1980-04-08 | Fuji Photo Film Co., Ltd. | Non-treatment type planographic printing plate materials |
CA1124248A (en) | 1978-08-27 | 1982-05-25 | Andrew A. Znotins | Method of making 5,6-dihydro-2-methyl-n-phenyl-1,4- oxathiin-3-carboxamide |
US4182716A (en) | 1978-09-05 | 1980-01-08 | Uniroyal, Ltd. | Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide |
CA1166262A (en) | 1981-08-11 | 1984-04-24 | Frederick M.M. Hager | Synthesis of intermediate for the manufacture of 5,6- dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamide |
IE56108B1 (en) * | 1982-07-16 | 1991-04-24 | Carpibem | 1-(2-carbalkoxy-4-(thienylcarboxamido)phenoxy)-3-amino 2-propanols,their preparation and applications thereof in therapeutics |
FR2530245A1 (fr) * | 1982-07-16 | 1984-01-20 | Carpibem | Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique |
JPS5951258A (ja) * | 1982-09-16 | 1984-03-24 | Sumitomo Chem Co Ltd | N−フエニルチオカ−バメ−ト系化合物、その製造法およびそれを有効成分とする農園芸用殺菌剤 |
BR8305022A (pt) * | 1982-09-16 | 1984-05-08 | Sumitomo Chemical Co | Composicao fungicida, n-fenilcarbamato, processo para controle de fungos patogenicos de plantas, uso do dito n - fenilcarbamato e processo para producao de tal n-fenilcarbamato |
FR2555179B1 (fr) * | 1983-11-21 | 1986-11-21 | Carpibem | Nouveaux (carbethoxy-2 furyl- ou benzofuryl-carboxamido-4 phenoxy)-1 amino-3 propanols-2 : leurs preparations et leurs applications en therapeutique |
AU570853B2 (en) * | 1985-08-26 | 1988-03-24 | United States of America, as represented by the Secretary, U.S. Department of Commerce, The | Inhibition of infectivity and cytopathic effect of htlv-111/ lav by purine bases |
DE3534440A1 (de) * | 1985-09-27 | 1987-04-02 | Hoechst Ag | Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes |
US4880782A (en) * | 1986-11-21 | 1989-11-14 | Max-Planck-Gesellschaft Zur Foederung Der Wissenschaften E.V. | Method of treating viral infections in humans and compositions therefor |
IT1222142B (it) * | 1987-07-27 | 1990-09-05 | Adolfo Turano | Composizioni farmaceutiche antivirali |
US4980371A (en) * | 1988-12-21 | 1990-12-25 | Merrell Dow Pharmaceuticals | Antiretroviral furan ketones |
-
1990
- 1990-09-26 US US07/588,208 patent/US5268389A/en not_active Expired - Lifetime
- 1990-10-09 DK DK90915588.9T patent/DK0497816T3/da active
- 1990-10-09 KR KR1019920700831A patent/KR100222233B1/ko not_active IP Right Cessation
- 1990-10-09 BR BR909007758A patent/BR9007758A/pt not_active Application Discontinuation
- 1990-10-09 WO PCT/US1990/005760 patent/WO1991005761A1/en active IP Right Grant
- 1990-10-09 DE DE69019533T patent/DE69019533T2/de not_active Expired - Fee Related
- 1990-10-09 AT AT90915588T patent/ATE122654T1/de not_active IP Right Cessation
- 1990-10-09 AU AU66035/90A patent/AU636409B2/en not_active Ceased
- 1990-10-09 HU HU9201258A patent/HU220759B1/hu unknown
- 1990-10-09 JP JP2514569A patent/JPH06102641B2/ja not_active Expired - Fee Related
- 1990-10-09 RU SU5011885A patent/RU2108785C1/ru not_active IP Right Cessation
- 1990-10-09 CA CA002067381A patent/CA2067381C/en not_active Expired - Fee Related
- 1990-10-09 EP EP90915588A patent/EP0497816B1/de not_active Expired - Lifetime
- 1990-10-10 IL IL9595690A patent/IL95956A/en not_active IP Right Cessation
- 1990-10-16 CN CN90108426A patent/CN1051036A/zh active Pending
-
1995
- 1995-06-07 US US08/485,291 patent/US5693827A/en not_active Expired - Lifetime
- 1995-08-16 GR GR950402247T patent/GR3017128T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
HUT60713A (en) | 1992-10-28 |
KR920703049A (ko) | 1992-12-17 |
CA2067381C (en) | 2004-04-06 |
AU6603590A (en) | 1991-05-16 |
CN1051036A (zh) | 1991-05-01 |
JPH04507422A (ja) | 1992-12-24 |
HU220759B1 (hu) | 2002-05-28 |
DK0497816T3 (da) | 1995-10-09 |
US5693827A (en) | 1997-12-02 |
CA2067381A1 (en) | 1991-04-17 |
IL95956A0 (en) | 1991-07-18 |
DE69019533D1 (de) | 1995-06-22 |
US5268389A (en) | 1993-12-07 |
EP0497816A1 (de) | 1992-08-12 |
KR100222233B1 (ko) | 1999-10-01 |
GR3017128T3 (en) | 1995-11-30 |
JPH06102641B2 (ja) | 1994-12-14 |
ATE122654T1 (de) | 1995-06-15 |
EP0497816B1 (de) | 1995-05-17 |
RU2108785C1 (ru) | 1998-04-20 |
AU636409B2 (en) | 1993-04-29 |
HU9201258D0 (en) | 1992-07-28 |
BR9007758A (pt) | 1992-08-11 |
WO1991005761A1 (en) | 1991-05-02 |
DE69019533T2 (de) | 1995-10-26 |
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