HRP930857A2 - New quinazolines as inhibitors of hiv reverse transcriptase - Google Patents
New quinazolines as inhibitors of hiv reverse transcriptase Download PDFInfo
- Publication number
- HRP930857A2 HRP930857A2 HR930857A HRP930857A HRP930857A2 HR P930857 A2 HRP930857 A2 HR P930857A2 HR 930857 A HR930857 A HR 930857A HR P930857 A HRP930857 A HR P930857A HR P930857 A2 HRP930857 A2 HR P930857A2
- Authority
- HR
- Croatia
- Prior art keywords
- chloro
- cyclopropyl
- dihydro
- quinazolin
- ethynyl
- Prior art date
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- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims description 12
- 239000003112 inhibitor Substances 0.000 title description 10
- 150000003246 quinazolines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 52
- -1 hydroxy, amino Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 208000030507 AIDS Diseases 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 208000031886 HIV Infections Diseases 0.000 claims description 11
- 208000037357 HIV infectious disease Diseases 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- VQWNFBGVGJSEIS-GOSISDBHSA-N (4s)-6-chloro-4-cyclopropyl-4-(2-pyridin-2-ylethynyl)-1,3-dihydroquinazolin-2-one Chemical compound C([C@]1(C2CC2)NC(=O)NC2=CC=C(C=C21)Cl)#CC1=CC=CC=N1 VQWNFBGVGJSEIS-GOSISDBHSA-N 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- VQWNFBGVGJSEIS-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(2-pyridin-2-ylethynyl)-1,3-dihydroquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)NC1(C1CC1)C#CC1=CC=CC=N1 VQWNFBGVGJSEIS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- HIDJVTANKWMNAG-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-3-methyl-4-(2-pyridin-2-ylethynyl)-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C1CC1)C#CC1=CC=CC=N1 HIDJVTANKWMNAG-UHFFFAOYSA-N 0.000 claims description 3
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- XEQHPIBWXHGKSY-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(4-fluorobut-1-ynyl)-3-methyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCCF)C1CC1 XEQHPIBWXHGKSY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- VJWHOIUEDKBQCF-UHFFFAOYSA-N 4-(3-azidoprop-1-ynyl)-6-chloro-4-cyclopropyl-3-methyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCN=[N+]=[N-])C1CC1 VJWHOIUEDKBQCF-UHFFFAOYSA-N 0.000 claims description 2
- PETGEEXEIYQVDC-UHFFFAOYSA-N 4-but-3-en-1-ynyl-6-chloro-4-cyclopropyl-3-methyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CC=C)C1CC1 PETGEEXEIYQVDC-UHFFFAOYSA-N 0.000 claims description 2
- IGRXUVJENYSECD-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-3-methyl-4-[3-(2,2,2-trifluoroethoxy)prop-1-ynyl]-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCOCC(F)(F)F)C1CC1 IGRXUVJENYSECD-UHFFFAOYSA-N 0.000 claims description 2
- PIAOOIFLDFDVCR-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(2-pyrazin-2-ylethynyl)-1,3-dihydroquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)NC1(C1CC1)C#CC1=CN=CC=N1 PIAOOIFLDFDVCR-UHFFFAOYSA-N 0.000 claims description 2
- DXQDLUHFSIHLID-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(2-pyridin-3-ylethynyl)-1,3-dihydroquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)NC1(C1CC1)C#CC1=CC=CN=C1 DXQDLUHFSIHLID-UHFFFAOYSA-N 0.000 claims description 2
- ZXBLZGVDNZXGPO-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(3-fluoroprop-1-ynyl)-3-methyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCF)C1CC1 ZXBLZGVDNZXGPO-UHFFFAOYSA-N 0.000 claims description 2
- BESHXIJJOSSCGD-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(3-hydroxyprop-1-ynyl)-3-methyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCO)C1CC1 BESHXIJJOSSCGD-UHFFFAOYSA-N 0.000 claims description 2
- YAISCFWDKKQPMO-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(3-imidazol-1-ylprop-1-ynyl)-3-methyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C1CC1)C#CCN1C=CN=C1 YAISCFWDKKQPMO-UHFFFAOYSA-N 0.000 claims description 2
- XDPOLXNKWSUAQD-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(3-methoxyprop-1-ynyl)-3-methyl-1h-quinazolin-2-one Chemical group CN1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCOC)C1CC1 XDPOLXNKWSUAQD-UHFFFAOYSA-N 0.000 claims description 2
- ASQHZXJWKBBVOO-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(4-fluorobut-1-ynyl)-1,3-dihydroquinazolin-2-one Chemical compound N1C(=O)NC2=CC=C(Cl)C=C2C1(C#CCCF)C1CC1 ASQHZXJWKBBVOO-UHFFFAOYSA-N 0.000 claims description 2
- BXKCPLKQZJHTRJ-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-[2-(2-nitrophenyl)ethynyl]-1,3-dihydroquinazolin-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C#CC1(C2CC2)C2=CC(Cl)=CC=C2NC(=O)N1 BXKCPLKQZJHTRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 239000011885 synergistic combination Substances 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 2
- JFCSLHTVEXFQHB-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-3-methyl-4-(3-morpholin-4-ylprop-1-ynyl)-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C1CC1)C#CCN1CCOCC1 JFCSLHTVEXFQHB-UHFFFAOYSA-N 0.000 claims 1
- BSQDJOLMDHVYDN-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-3-methyl-4-(3-pyridin-2-yloxyprop-1-ynyl)-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(C1CC1)C#CCOC1=CC=CC=N1 BSQDJOLMDHVYDN-UHFFFAOYSA-N 0.000 claims 1
- SIBNNEGLGGVEQO-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(2-pyridin-4-ylethynyl)-1,3-dihydroquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)NC1(C1CC1)C#CC1=CC=NC=C1 SIBNNEGLGGVEQO-UHFFFAOYSA-N 0.000 claims 1
- HVBIKFMINXGRGX-UHFFFAOYSA-N 6-chloro-4-cyclopropyl-4-(2-pyrimidin-5-ylethynyl)-1,3-dihydroquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)NC1(C1CC1)C#CC1=CN=CN=C1 HVBIKFMINXGRGX-UHFFFAOYSA-N 0.000 claims 1
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- 235000019634 flavors Nutrition 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000000833 heterodimer Substances 0.000 description 1
- 239000004030 hiv protease inhibitor Substances 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- VFZXMEQGIIWBFJ-UHFFFAOYSA-M magnesium;cyclopropane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]1 VFZXMEQGIIWBFJ-UHFFFAOYSA-M 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 102000013415 peroxidase activity proteins Human genes 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 108700004029 pol Genes Proteins 0.000 description 1
- 101150088264 pol gene Proteins 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000010839 reverse transcription Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88011992A | 1992-05-07 | 1992-05-07 | |
| US99116492A | 1992-12-16 | 1992-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP930857A2 true HRP930857A2 (en) | 1995-06-30 |
Family
ID=27128564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR930857A HRP930857A2 (en) | 1992-05-07 | 1993-05-05 | New quinazolines as inhibitors of hiv reverse transcriptase |
Country Status (15)
| Country | Link |
|---|---|
| EP (2) | EP0639184A1 (de) |
| JP (1) | JPH0813805B2 (de) |
| KR (1) | KR950701322A (de) |
| CN (1) | CN1085550A (de) |
| AU (2) | AU4220493A (de) |
| BG (1) | BG99149A (de) |
| CA (1) | CA2095194A1 (de) |
| CZ (1) | CZ272494A3 (de) |
| FI (1) | FI945199A (de) |
| HR (1) | HRP930857A2 (de) |
| HU (1) | HUT71401A (de) |
| IL (1) | IL105551A0 (de) |
| MX (1) | MX9302681A (de) |
| SI (1) | SI9300244A (de) |
| WO (1) | WO1993022292A1 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2281297A (en) * | 1993-08-27 | 1995-03-01 | Merck & Co Inc | Quinazoline compounds |
| US5434152A (en) * | 1993-11-08 | 1995-07-18 | Merck & Co., Inc. | Asymmetric synthesis of (S)-(-)-6-chloro-4- cyclopropyl-3,4-dihydro-4-[(2-pyridyl)ethynyl]-2(1H)-quinazolinone |
| HRP980143A2 (en) * | 1997-04-09 | 1999-02-28 | Soo Sung Ko | 4,4-disubstituted-3,4-dihydro-2 (1h)-quinazolinones useful as hiv reverse transcriptase inhibitors |
| US6124302A (en) | 1997-04-09 | 2000-09-26 | Dupont Pharmaceuticals | 4,4-disubstituted-3,4-dihydro-2(1H)-quinazolinones useful as HIV reverse transcriptase inhibitors |
| AU4719799A (en) * | 1998-06-30 | 2000-01-17 | Du Pont Pharmaceuticals Company | Substituted quinolin-2(1h)-ones useful as hiv reverse transcriptase inhibitors |
| EP1183242A2 (de) | 1999-05-26 | 2002-03-06 | Du Pont Pharmaceuticals Company | Als hemmer der reversen transcriptase von hiv verwendbare 1,4-benzodiazepin-2-one |
| CA2377629A1 (en) * | 2000-04-25 | 2001-11-08 | Hae-Young Bae | Biphenyl butyric acid derivative as a matrix metalloproteinase inhibitor |
| US7119111B2 (en) | 2002-05-29 | 2006-10-10 | Amgen, Inc. | 2-oxo-1,3,4-trihydroquinazolinyl derivatives and methods of use |
| JP5470043B2 (ja) * | 2007-10-05 | 2014-04-16 | Ｍｓｄ株式会社 | ベンゾオキサジノン誘導体 |
| CN101544630B (zh) * | 2009-05-13 | 2013-03-13 | 中国科学院广州生物医药与健康研究院 | 羟基化茚地那韦的制备方法 |
| EP3317278B1 (de) | 2015-07-01 | 2021-04-14 | Crinetics Pharmaceuticals, Inc. | Somatostatinmodulatoren und verwendungen davon |
| JOP20180009A1 (ar) | 2017-02-06 | 2019-01-30 | Gilead Sciences Inc | مركبات مثبط فيروس hiv |
| EP3658560A4 (de) | 2017-07-25 | 2021-01-06 | Crinetics Pharmaceuticals, Inc. | Somatostatinmodulatoren und verwendungen davon |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL147140B (nl) * | 1968-11-26 | 1975-09-15 | Farmaceutici Italia | Werkwijze voor het bereiden van geneesmiddelen met een remmende werking op het centrale zenuwstelsel. |
| IL102764A0 (en) * | 1991-08-16 | 1993-01-31 | Merck & Co Inc | Quinazoline derivatives,and pharmaceutical compositions containing them |
-
1993
- 1993-04-28 HU HU9403187A patent/HUT71401A/hu unknown
- 1993-04-28 AU AU42204/93A patent/AU4220493A/en not_active Abandoned
- 1993-04-28 EP EP93910860A patent/EP0639184A1/de not_active Withdrawn
- 1993-04-28 WO PCT/US1993/003975 patent/WO1993022292A1/en not_active Application Discontinuation
- 1993-04-28 KR KR1019940703948A patent/KR950701322A/ko not_active Application Discontinuation
- 1993-04-28 CZ CZ942724A patent/CZ272494A3/cs unknown
- 1993-04-29 CA CA002095194A patent/CA2095194A1/en not_active Abandoned
- 1993-04-29 IL IL105551A patent/IL105551A0/xx unknown
- 1993-04-29 EP EP93201232A patent/EP0569083A1/de not_active Withdrawn
- 1993-05-05 HR HR930857A patent/HRP930857A2/hr not_active Application Discontinuation
- 1993-05-06 CN CN93107074A patent/CN1085550A/zh active Pending
- 1993-05-06 MX MX9302681A patent/MX9302681A/es unknown
- 1993-05-06 AU AU38413/93A patent/AU3841393A/en not_active Abandoned
- 1993-05-07 SI SI9300244A patent/SI9300244A/sl unknown
- 1993-05-07 JP JP5107015A patent/JPH0813805B2/ja not_active Expired - Lifetime
-
1994
- 1994-10-31 BG BG99149A patent/BG99149A/xx unknown
- 1994-11-04 FI FI945199A patent/FI945199A/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0813805B2 (ja) | 1996-02-14 |
| HUT71401A (en) | 1995-11-28 |
| AU4220493A (en) | 1993-11-29 |
| KR950701322A (ko) | 1995-03-23 |
| FI945199A0 (fi) | 1994-11-04 |
| JPH069578A (ja) | 1994-01-18 |
| IL105551A0 (en) | 1993-08-18 |
| EP0569083A1 (de) | 1993-11-10 |
| FI945199A (fi) | 1994-11-04 |
| WO1993022292A1 (en) | 1993-11-11 |
| AU3841393A (en) | 1993-11-11 |
| EP0639184A1 (de) | 1995-02-22 |
| CN1085550A (zh) | 1994-04-20 |
| BG99149A (en) | 1995-06-30 |
| MX9302681A (es) | 1994-05-31 |
| CA2095194A1 (en) | 1993-11-08 |
| CZ272494A3 (en) | 1995-10-18 |
| SI9300244A (sl) | 1993-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ODBC | Application rejected |