HRP980482A2 - 5,5-disubstituted-1,5-dihydro-4,1-benzoxazepin-2(3h)-ones useful as hiv reverse transcriptase inhibitors - Google Patents
5,5-disubstituted-1,5-dihydro-4,1-benzoxazepin-2(3h)-ones useful as hiv reverse transcriptase inhibitorsInfo
- Publication number
- HRP980482A2 HRP980482A2 HR60/057,431A HRP980482A HRP980482A2 HR P980482 A2 HRP980482 A2 HR P980482A2 HR P980482 A HRP980482 A HR P980482A HR P980482 A2 HRP980482 A2 HR P980482A2
- Authority
- HR
- Croatia
- Prior art keywords
- dihydro
- trifluoromethyl
- benzoxazepin
- chloro
- rel
- Prior art date
Links
- -1 5,5-disubstituted-1,5-dihydro-4,1-benzoxazepin-2(3h)-ones Chemical class 0.000 title claims description 54
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title claims description 23
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 203
- 238000000034 method Methods 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 229910052740 iodine Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000003112 inhibitor Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 14
- 208000031886 HIV Infections Diseases 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 13
- 208000037357 HIV infectious disease Diseases 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229960001936 indinavir Drugs 0.000 claims description 7
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 6
- 239000002777 nucleoside Substances 0.000 claims description 6
- 229960000311 ritonavir Drugs 0.000 claims description 6
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 6
- 229910052701 rubidium Inorganic materials 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- UZQLDBWLAOCBOO-YMWZRXTESA-N (3s,5s)-7-chloro-5-[(e)-2-cyclopropylethenyl]-3-methyl-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound C(/[C@@]1(O[C@H](C(NC2=CC=C(Cl)C=C21)=O)C)C(F)(F)F)=C\C1CC1 UZQLDBWLAOCBOO-YMWZRXTESA-N 0.000 claims description 5
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 5
- 229910004013 NO 2 Inorganic materials 0.000 claims description 5
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 5
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000004030 hiv protease inhibitor Substances 0.000 claims description 5
- 229960000884 nelfinavir Drugs 0.000 claims description 5
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 5
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical group C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 5
- 229960001852 saquinavir Drugs 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 4
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- OQTHCVVSOBEPGF-UHFFFAOYSA-N 1-ethynyl-7-fluoro-5-propan-2-yl-5-(trifluoromethyl)-4,1-benzoxazepin-2-one Chemical compound CC(C)C1(C(F)(F)F)OCC(=O)N(C#C)C2=CC=C(F)C=C12 OQTHCVVSOBEPGF-UHFFFAOYSA-N 0.000 claims description 4
- OQDAUOCJFHPSRU-UHFFFAOYSA-N 5-but-1-ynyl-7-chloro-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CCC#CC1(C(F)(F)F)OCC(=O)NC2=CC=C(Cl)C=C12 OQDAUOCJFHPSRU-UHFFFAOYSA-N 0.000 claims description 4
- KEAWUGALLLUBLJ-UHFFFAOYSA-N 5-butyl-7-chloro-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CCCCC1(C(F)(F)F)OCC(=O)NC2=CC=C(Cl)C=C12 KEAWUGALLLUBLJ-UHFFFAOYSA-N 0.000 claims description 4
- NFSDYWBEIJLYRK-UHFFFAOYSA-N 7-chloro-5-(3-methylbut-1-ynyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CC(C)C#CC1(C(F)(F)F)OCC(=O)NC2=CC=C(Cl)C=C12 NFSDYWBEIJLYRK-UHFFFAOYSA-N 0.000 claims description 4
- RIFHBKAORDJJNW-AATRIKPKSA-N 7-chloro-5-[(e)-2-cyclopropylethenyl]-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound O1CC(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)\C=C\C1CC1 RIFHBKAORDJJNW-AATRIKPKSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 4
- 108091008648 NR7C Proteins 0.000 claims description 4
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 4
- 229960003804 efavirenz Drugs 0.000 claims description 4
- 229940063627 rescriptor Drugs 0.000 claims description 4
- QCTDQQNLOPRRMO-VFZGTOFNSA-N (3s,5s)-7-chloro-5-(2-cyclopropylethynyl)-3-methyl-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound C([C@@]1(O[C@H](C(NC2=CC=C(Cl)C=C21)=O)C)C(F)(F)F)#CC1CC1 QCTDQQNLOPRRMO-VFZGTOFNSA-N 0.000 claims description 3
- NFSDYWBEIJLYRK-AWEZNQCLSA-N (5s)-7-chloro-5-(3-methylbut-1-ynyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CC(C)C#C[C@]1(C(F)(F)F)OCC(=O)NC2=CC=C(Cl)C=C12 NFSDYWBEIJLYRK-AWEZNQCLSA-N 0.000 claims description 3
- XVUOMGDBNNHRNX-UHFFFAOYSA-N 1-ethynyl-5,6-difluoro-4-propan-2-yl-4-(trifluoromethyl)-3,1-benzoxazin-2-one Chemical compound C1=C(F)C(F)=C2C(C(C)C)(C(F)(F)F)OC(=O)N(C#C)C2=C1 XVUOMGDBNNHRNX-UHFFFAOYSA-N 0.000 claims description 3
- UHBMRVAHGUULGY-AATRIKPKSA-N 6,7-difluoro-5-[(e)-3-methylbut-1-enyl]-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CC(C)\C=C\C1(C(F)(F)F)OCC(=O)NC2=CC=C(F)C(F)=C12 UHBMRVAHGUULGY-AATRIKPKSA-N 0.000 claims description 3
- ODHBANPGOOUTBK-UHFFFAOYSA-N 7-chloro-1-ethynyl-5-propan-2-yl-5-(trifluoromethyl)-4,1-benzoxazepin-2-one Chemical compound CC(C)C1(C(F)(F)F)OCC(=O)N(C#C)C2=CC=C(Cl)C=C12 ODHBANPGOOUTBK-UHFFFAOYSA-N 0.000 claims description 3
- ZMIOLCLUEBCNKV-UHFFFAOYSA-N 7-chloro-5-(2-phenylethynyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound O1CC(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1=CC=CC=C1 ZMIOLCLUEBCNKV-UHFFFAOYSA-N 0.000 claims description 3
- QACTVSADKHGKOD-UHFFFAOYSA-N 7-chloro-5-(2-pyridin-3-ylethynyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound O1CC(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1=CC=CN=C1 QACTVSADKHGKOD-UHFFFAOYSA-N 0.000 claims description 3
- UGBUQZIOUQEOKX-AATRIKPKSA-N 7-chloro-5-[(e)-3-methylbut-1-enyl]-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CC(C)\C=C\C1(C(F)(F)F)OCC(=O)NC2=CC=C(Cl)C=C12 UGBUQZIOUQEOKX-AATRIKPKSA-N 0.000 claims description 3
- XVYHYKDKUGPDNG-UHFFFAOYSA-N 7-fluoro-5-(3-methylbutyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CC(C)CCC1(C(F)(F)F)OCC(=O)NC2=CC=C(F)C=C12 XVYHYKDKUGPDNG-UHFFFAOYSA-N 0.000 claims description 3
- KZBHOHZAFNZDTN-AATRIKPKSA-N 7-fluoro-5-[(e)-3-methylbut-1-enyl]-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound CC(C)\C=C\C1(C(F)(F)F)OCC(=O)NC2=CC=C(F)C=C12 KZBHOHZAFNZDTN-AATRIKPKSA-N 0.000 claims description 3
- VJIJJLGZKFMVSO-UHFFFAOYSA-N 7-methoxy-5-(3-methylbutyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound N1C(=O)COC(CCC(C)C)(C(F)(F)F)C2=CC(OC)=CC=C21 VJIJJLGZKFMVSO-UHFFFAOYSA-N 0.000 claims description 3
- NJBBLOIWMSYVCQ-VZTVMPNDSA-N Kynostatin 272 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 NJBBLOIWMSYVCQ-VZTVMPNDSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 claims description 3
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- VCYQENLVFRTJIC-UHFFFAOYSA-N 4-cyano-n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]benzenesulfonamide Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C#N)C=CC=1)C1CC1 VCYQENLVFRTJIC-UHFFFAOYSA-N 0.000 claims description 2
- STDUMDNEHXHPDZ-UHFFFAOYSA-N 7-chloro-5-(2-cyclopropylethynyl)-5-(trifluoromethyl)-1h-4,1-benzoxazepin-2-one Chemical compound O1CC(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 STDUMDNEHXHPDZ-UHFFFAOYSA-N 0.000 claims description 2
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- WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical class C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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- 150000003556 thioamides Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
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- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D413/06—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 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5743197P | 1997-09-02 | 1997-09-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP980482A2 true HRP980482A2 (en) | 1999-10-31 |
Family
ID=22010528
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR60/057,431A HRP980482A2 (en) | 1997-09-02 | 1998-09-01 | 5,5-disubstituted-1,5-dihydro-4,1-benzoxazepin-2(3h)-ones useful as hiv reverse transcriptase inhibitors |
Country Status (12)
Country | Link |
---|---|
US (2) | US6140320A (xx) |
EP (1) | EP1009742A1 (xx) |
JP (1) | JP2001514256A (xx) |
CN (1) | CN1268944A (xx) |
AR (1) | AR015163A1 (xx) |
AU (1) | AU9023998A (xx) |
BR (1) | BR9814933A (xx) |
CA (1) | CA2303295A1 (xx) |
HR (1) | HRP980482A2 (xx) |
TW (1) | TW564248B (xx) |
WO (1) | WO1999011635A1 (xx) |
ZA (1) | ZA987539B (xx) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6943097B2 (en) * | 2003-08-19 | 2005-09-13 | International Business Machines Corporation | Atomic layer deposition of metallic contacts, gates and diffusion barriers |
US20070037894A1 (en) * | 2003-09-19 | 2007-02-15 | Hahnfeld Jerry L | Multifunctional menomers and polyarylene compsotions therefrom |
EP1666066A4 (en) * | 2003-09-19 | 2007-03-28 | Eisai R&D Man Co Ltd | DRUG AGAINST THE DOWN SYNDROME |
US7323455B2 (en) | 2004-03-24 | 2008-01-29 | Wyeth | 7-aryl 1,5-dihydro-4,1-benzoxazepin-2(3H)-one derivatives and their use as progesterone receptor modulators |
CN103254087B (zh) * | 2013-06-07 | 2015-03-18 | 郑州大学 | 依非韦伦中间体的制备方法 |
WO2023192430A1 (en) * | 2022-03-30 | 2023-10-05 | University Of Florida Research Foundation, Incorported | Compounds for treating psychostimulant misuse |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4374842A (en) * | 1980-04-18 | 1983-02-22 | Shionogi & Co., Ltd. | 4,1-Benzoxazepines and compositions |
EP0142361B1 (en) * | 1983-11-17 | 1988-05-11 | The Upjohn Company | N-substituted-5-phenyl-4,1-benzoxazepin-2(3h)-ones having therapeutic utility |
EP0417534A1 (en) * | 1989-08-29 | 1991-03-20 | Boehringer Ingelheim Pharmaceuticals Inc. | Pyrido[2,3-b][1,4]benzoxazepin (and thiazepin)-6(5H)-ones and thiones and their use in the prevention or treatment of AIDS |
SG48855A1 (en) * | 1992-04-20 | 1998-05-18 | Takeda Chemical Industries Ltd | 4,1-benzoxazepin derivatives and their use |
US5665720A (en) * | 1992-08-07 | 1997-09-09 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
WO1995020389A1 (en) * | 1994-01-28 | 1995-08-03 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
JPH08259447A (ja) * | 1995-03-24 | 1996-10-08 | Takeda Chem Ind Ltd | コレシストキニン拮抗剤 |
ATE248826T1 (de) * | 1996-10-02 | 2003-09-15 | Bristol Myers Squibb Pharma Co | 4,4-disubstituierte 1,4-dihydro-2h-3,1-benzoxazin-2-one die anwendbar sind als hiv- reverstranskriptase-inhibitoren, zwischenprodukte und verfahren zu ihrer herstellung |
-
1998
- 1998-08-19 CN CN98808673A patent/CN1268944A/zh active Pending
- 1998-08-19 AU AU90239/98A patent/AU9023998A/en not_active Abandoned
- 1998-08-19 BR BR9814933-4A patent/BR9814933A/pt not_active IP Right Cessation
- 1998-08-19 WO PCT/US1998/017155 patent/WO1999011635A1/en not_active Application Discontinuation
- 1998-08-19 EP EP98942117A patent/EP1009742A1/en not_active Withdrawn
- 1998-08-19 JP JP2000508674A patent/JP2001514256A/ja active Pending
- 1998-08-19 CA CA002303295A patent/CA2303295A1/en not_active Abandoned
- 1998-08-20 ZA ZA9807539A patent/ZA987539B/xx unknown
- 1998-08-29 TW TW087114348A patent/TW564248B/zh active
- 1998-09-01 US US09/145,101 patent/US6140320A/en not_active Expired - Lifetime
- 1998-09-01 HR HR60/057,431A patent/HRP980482A2/hr not_active Application Discontinuation
- 1998-09-02 AR ARP980104379A patent/AR015163A1/es unknown
-
2000
- 2000-09-07 US US09/657,518 patent/US6489320B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
AR015163A1 (es) | 2001-04-18 |
WO1999011635A1 (en) | 1999-03-11 |
US6489320B1 (en) | 2002-12-03 |
US6140320A (en) | 2000-10-31 |
AU9023998A (en) | 1999-03-22 |
JP2001514256A (ja) | 2001-09-11 |
TW564248B (en) | 2003-12-01 |
BR9814933A (pt) | 2001-01-30 |
ZA987539B (en) | 2000-02-21 |
EP1009742A1 (en) | 2000-06-21 |
CA2303295A1 (en) | 1999-03-11 |
CN1268944A (zh) | 2000-10-04 |
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