NO329676B1 - Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat - Google Patents
Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat Download PDFInfo
- Publication number
- NO329676B1 NO329676B1 NO20010282A NO20010282A NO329676B1 NO 329676 B1 NO329676 B1 NO 329676B1 NO 20010282 A NO20010282 A NO 20010282A NO 20010282 A NO20010282 A NO 20010282A NO 329676 B1 NO329676 B1 NO 329676B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- water
- producing
- solvent
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- -1 (4-aminophenyl) sulfonyl Chemical group 0.000 title description 11
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 title description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title description 6
- 239000011575 calcium Substances 0.000 title description 5
- 229910052791 calcium Inorganic materials 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 35
- 239000011928 denatured alcohol Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910001424 calcium ion Inorganic materials 0.000 claims description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- 238000003306 harvesting Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 230000000865 phosphorylative effect Effects 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 239000001639 calcium acetate Substances 0.000 claims description 6
- 229960005147 calcium acetate Drugs 0.000 claims description 6
- 235000011092 calcium acetate Nutrition 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 208000005074 Retroviridae Infections Diseases 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- CDRQNDUZTKTSBS-NHALQGLQSA-L calcium;n-[(2s,3r,4s)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-cyclohex-2-en-1-yl-4-(furan-2-yl)-3-phosphonooxybutan-2-yl]carbamate Chemical compound [Ca+2].C([C@@H]([C@@H](OP(O)(O)=O)[C@H](N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C=1OC=CC=1)NC([O-])=O)C1CCCC=C1.C([C@@H]([C@@H](OP(O)(O)=O)[C@H](N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C=1OC=CC=1)NC([O-])=O)C1CCCC=C1 CDRQNDUZTKTSBS-NHALQGLQSA-L 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical group [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000013160 medical therapy Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 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 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 229960001830 amprenavir Drugs 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- XQKKWWCELHKGKB-UHFFFAOYSA-L calcium acetate monohydrate Chemical compound O.[Ca+2].CC([O-])=O.CC([O-])=O XQKKWWCELHKGKB-UHFFFAOYSA-L 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- XOGQXKBFJZURRD-HQROKSDRSA-N calcium;[(3s)-oxolan-3-yl] n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate Chemical compound [Ca].C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 XOGQXKBFJZURRD-HQROKSDRSA-N 0.000 description 6
- 239000004030 hiv protease inhibitor Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 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 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- GWKIPRVERALPRD-ZDUSSCGKSA-N (s)-4-isopropoxycarbonyl-6-methoxy-3-methylthiomethyl-3,4-dihydroquinoxalin-2(1h)-thione Chemical compound N1C(=S)[C@H](CSC)N(C(=O)OC(C)C)C2=CC(OC)=CC=C21 GWKIPRVERALPRD-ZDUSSCGKSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- 229940122440 HIV protease inhibitor Drugs 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 102000014961 Protein Precursors Human genes 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YADJFRGSGWGMNH-UHFFFAOYSA-N [chloro(phenylmethoxy)phosphoryl]oxymethylbenzene Chemical compound C=1C=CC=CC=1COP(=O)(Cl)OCC1=CC=CC=C1 YADJFRGSGWGMNH-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical class C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 description 1
- HDMHBHNRWDNNCD-UHFFFAOYSA-N 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine Chemical compound OCCOCN1C(=O)NC(=O)C(C)=C1SC1=CC=CC=C1 HDMHBHNRWDNNCD-UHFFFAOYSA-N 0.000 description 1
- ASOMNDIOOKDVDC-UHFFFAOYSA-N 1h-indol-2-yl-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 ASOMNDIOOKDVDC-UHFFFAOYSA-N 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- 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 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 238000012369 In process control Methods 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 1
- 208000008771 Lymphadenopathy Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229940124821 NNRTIs Drugs 0.000 description 1
- KBGHCNOQBKTDTH-UHFFFAOYSA-N OC(=O)P(=O)=O Chemical compound OC(=O)P(=O)=O KBGHCNOQBKTDTH-UHFFFAOYSA-N 0.000 description 1
- 206010033885 Paraparesis Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108010078762 Protein Precursors Proteins 0.000 description 1
- 206010038997 Retroviral infections Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 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 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 1
- 206010043561 Thrombocytopenic purpura Diseases 0.000 description 1
- 108700022715 Viral Proteases Proteins 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZMNCIAGFQBUWTJ-OEMFJLHTSA-N [(3s)-oxolan-3-yl] n-[(2s,3r)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 ZMNCIAGFQBUWTJ-OEMFJLHTSA-N 0.000 description 1
- HHEVDQQNXOSEBD-OEMFJLHTSA-N [(3s)-oxolan-3-yl] n-[(2s,3r)-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 HHEVDQQNXOSEBD-OEMFJLHTSA-N 0.000 description 1
- JARNKPQDFXUJTE-UHFFFAOYSA-N [3-hydroxy-5-[[3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]butanoyl]amino]-1,6-diphenylhexan-2-yl]carbamic acid Chemical compound C=1C=CC=CC=1CC(NC(O)=O)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 JARNKPQDFXUJTE-UHFFFAOYSA-N 0.000 description 1
- 229960004748 abacavir Drugs 0.000 description 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940067460 calcium acetate monohydrate Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229960002656 didanosine Drugs 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000007919 dispersible tablet Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 150000005233 imidazopyridazines Chemical class 0.000 description 1
- 238000010965 in-process control Methods 0.000 description 1
- 229960001936 indinavir Drugs 0.000 description 1
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- KELNNWMENBUHNS-NSHDSACASA-N isopropyl (2s)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxaline-1(2h)-carboxylate Chemical compound FC1=CC=C2NC(=O)[C@H](CC)N(C(=O)OC(C)C)C2=C1 KELNNWMENBUHNS-NSHDSACASA-N 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- CJPLEFFCVDQQFZ-UHFFFAOYSA-N loviride Chemical compound CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-UHFFFAOYSA-N 0.000 description 1
- 229950006243 loviride Drugs 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 229960000884 nelfinavir Drugs 0.000 description 1
- 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 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229960000689 nevirapine Drugs 0.000 description 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 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
- 230000005855 radiation Effects 0.000 description 1
- 229960000311 ritonavir Drugs 0.000 description 1
- 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 description 1
- 229960001852 saquinavir Drugs 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound 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 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000006514 viral protein processing Effects 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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 Table
- 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
-
- 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 Table
- 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
- C07F9/65515—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 five-membered ring
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9815567.4A GB9815567D0 (en) | 1998-07-18 | 1998-07-18 | Antiviral compound |
| PCT/EP1999/004991 WO2000004033A1 (en) | 1998-07-18 | 1999-07-15 | Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino] -1-benzyl-2- (phosphonooxy) propylcarbamate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010282D0 NO20010282D0 (no) | 2001-01-17 |
| NO20010282L NO20010282L (no) | 2001-03-07 |
| NO329676B1 true NO329676B1 (no) | 2010-11-29 |
Family
ID=10835689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010282A NO329676B1 (no) | 1998-07-18 | 2001-01-17 | Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat |
Country Status (47)
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9914821D0 (en) * | 1999-06-24 | 1999-08-25 | Glaxo Group Ltd | Compounds |
| CZ300031B6 (cs) * | 1999-10-06 | 2009-01-14 | Tibotec Pharmaceuticals Ltd. | Hexahydrofuro[2,3-b]furan-3-yl-N-{3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl)amino]-1-benzyl-2-hydroxypropyl}karbamát a farmaceutický prípravek s jeho obsahem |
| DE60017180T2 (de) * | 1999-10-08 | 2005-12-08 | Affinium Pharmaceuticals, Inc., Toronto | Fab i inhibitoren |
| CA2444597A1 (en) * | 2001-04-06 | 2002-10-06 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| EP1501841A2 (en) | 2002-04-26 | 2005-02-02 | Gilead Sciences, Inc. | Non nucleoside reverse transcriptase inhibitors |
| ES2518316T3 (es) | 2002-12-06 | 2014-11-05 | Debiopharm International Sa | Compuestos heterocíclicos, métodos de fabricación de los mismos y su uso en terapia |
| EP1608377B1 (en) | 2003-03-17 | 2008-10-01 | Affinium Pharmaceuticals, Inc. | Pharmaceutical compositions comprising inhibitors of fab i and further antibiotics |
| WO2005002626A2 (en) | 2003-04-25 | 2005-01-13 | Gilead Sciences, Inc. | Therapeutic phosphonate compounds |
| US7407965B2 (en) | 2003-04-25 | 2008-08-05 | Gilead Sciences, Inc. | Phosphonate analogs for treating metabolic diseases |
| US7427636B2 (en) | 2003-04-25 | 2008-09-23 | Gilead Sciences, Inc. | Inosine monophosphate dehydrogenase inhibitory phosphonate compounds |
| US7452901B2 (en) | 2003-04-25 | 2008-11-18 | Gilead Sciences, Inc. | Anti-cancer phosphonate analogs |
| EP1628685B1 (en) | 2003-04-25 | 2010-12-08 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| US7470724B2 (en) | 2003-04-25 | 2008-12-30 | Gilead Sciences, Inc. | Phosphonate compounds having immuno-modulatory activity |
| US7300924B2 (en) | 2003-04-25 | 2007-11-27 | Gilead Sciences, Inc. | Anti-infective phosphonate analogs |
| US7432261B2 (en) | 2003-04-25 | 2008-10-07 | Gilead Sciences, Inc. | Anti-inflammatory phosphonate compounds |
| MXPA05011296A (es) | 2003-04-25 | 2006-01-24 | Gilead Sciences Inc | Conjugados de fosfonato inhibidores de la cinasa. |
| ES2297467T3 (es) * | 2003-09-30 | 2008-05-01 | Tibotec Pharmaceuticals Ltd. | Sulfonamidas de inhibicion de vhc. |
| WO2005044279A1 (en) | 2003-10-24 | 2005-05-19 | Gilead Sciences, Inc. | Purine nucleoside phosphonate conjugates |
| JP2007508843A (ja) | 2003-10-24 | 2007-04-12 | ギリアード サイエンシーズ， インコーポレイテッド | 治療用化合物の同定のための方法および組成物 |
| US7432273B2 (en) | 2003-10-24 | 2008-10-07 | Gilead Sciences, Inc. | Phosphonate analogs of antimetabolites |
| EP1706405B1 (en) | 2003-12-22 | 2009-03-04 | Gilead Sciences, Inc. | 4'-substituted carbovir- and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity |
| SI1828167T1 (sl) * | 2004-06-04 | 2014-12-31 | Debiopharm International Sa Forum "Apres-Demain" | Akrilamidni derivati kot anitibiotična sredstva |
| DK1778251T3 (da) | 2004-07-27 | 2011-07-18 | Gilead Sciences Inc | Nukleosidphosphatkonjugater som anti-HIV-midler |
| PL1824563T3 (pl) | 2004-11-26 | 2010-07-30 | Ucl Business Plc | Kompozycje zawierające ornitynę i fenylooctan lub fenylomaślan do leczenia encefalopatii wątrobowej |
| CA2632476A1 (en) * | 2005-12-05 | 2007-06-14 | Affinium Pharmaceuticals, Inc. | Heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents |
| CA2658506C (en) | 2006-07-20 | 2016-01-26 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab 1 inhibitors |
| EP3255045A1 (en) | 2007-02-16 | 2017-12-13 | Debiopharm International SA | Salts, prodrugs and polymorphs of fab i inhibitors |
| KR101518079B1 (ko) | 2007-03-12 | 2015-05-06 | 넥타르 테라퓨틱스 | 올리고머-프로테아제 억제제 컨주게이트 |
| US9095620B2 (en) * | 2008-03-12 | 2015-08-04 | Nektar Therapeutics | Reagents |
| WO2010005986A1 (en) | 2008-07-08 | 2010-01-14 | Gilead Sciences, Inc. | Salts of hiv inhibitor compounds |
| NO2413924T3 (cs) | 2009-04-03 | 2018-02-24 | ||
| WO2010134045A1 (en) * | 2009-05-20 | 2010-11-25 | Ranbaxy Laboratories Limited | Amorphous fosamprenavir calcium |
| EP3517110A1 (en) | 2009-06-08 | 2019-07-31 | UCL Business PLC | Treatment of inflammation using l-ornithine phenylacetate |
| WO2010144869A2 (en) | 2009-06-12 | 2010-12-16 | Nektar Therapeutics | Protease inhibitors |
| EP2448949A1 (en) | 2009-06-30 | 2012-05-09 | Ranbaxy Laboratories Limited | Crystalline form of fosamprenavir calcium |
| WO2011033469A1 (en) | 2009-09-16 | 2011-03-24 | Ranbaxy Laboratories Limited | Process for the preparation of fosamprenavir calcium |
| US20110165202A1 (en) * | 2010-01-07 | 2011-07-07 | Pliva Hrvatska D.O.O. | Solid state forms of fosamprenavir calcium salt and processes for preparation thereof |
| EP3127542B1 (en) | 2010-01-27 | 2018-08-22 | VIIV Healthcare Company | Antiviral therapy |
| US20110224443A1 (en) * | 2010-03-15 | 2011-09-15 | Venkata Naga Brahmeshwara Rao Mandava | Preparation of fosamprenavir calcium |
| WO2011114212A1 (en) | 2010-03-19 | 2011-09-22 | Lupin Limited | Ammonium, calcium and tris salts of fosamprenavir |
| WO2011158259A1 (en) | 2010-06-18 | 2011-12-22 | Matrix Laboratories Ltd | Novel process for the preparation of (3s)-tetrahydrofuran-3-yl (is, 2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-(phosphonooxy) propylcarbamate and its pharmaceutically acceptable salts thereof |
| US8877947B2 (en) | 2010-09-10 | 2014-11-04 | Lupin Limited | Process for preparation of substantially pure fosamprenavir calcium and its intermediates |
| AU2011312042B2 (en) | 2010-10-06 | 2015-08-20 | Ocera Therapeutics, Inc. | Methods of making L-ornithine phenyl acetate |
| CN102453054B (zh) * | 2010-10-29 | 2015-06-10 | 浙江九洲药业股份有限公司 | 一种福沙那韦衍生物的制备方法及相关中间体 |
| CN102453053B (zh) * | 2010-10-29 | 2014-11-26 | 浙江九洲药业股份有限公司 | 一种福沙那韦钙晶体及其制备方法 |
| WO2012085625A1 (en) | 2010-12-21 | 2012-06-28 | Lupin Limited | Process for the preparation of fosamprenavir calcium and intermediate used in its preparation |
| WO2012107937A2 (en) * | 2011-02-10 | 2012-08-16 | Mylan Laboratories Ltd | Crystalline fosamprenavir calcium and process for the preparation thereof" |
| WO2013011485A1 (en) | 2011-07-20 | 2013-01-24 | Ranbaxy Laboratories Limited | Process for the preparation of sulfonamides useful as retroviral protease inhibitors |
| US9233943B2 (en) | 2012-01-10 | 2016-01-12 | Council Of Scientific & Industrial Research | Process for synthesis of syn azido epdxide and its use as intermediate for the synthesis of amprenavir and saquinavir |
| TR201909016T4 (tr) | 2012-06-19 | 2019-07-22 | Debiopharm Int Sa | (E)-n-metil-n-((3-metilbenzofuran-2-il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamidin ön ilaç türevleri. |
| EP3685841A1 (en) | 2014-11-24 | 2020-07-29 | Ucl Business Ltd | Treatment of diseases associated with hepatic stellate cell activation using ammonia-lowering therapies |
| CA2995823A1 (en) | 2015-08-18 | 2017-02-23 | Ocera Therapeutics, Inc. | Treatment and prevention of muscle loss using l-ornithine in combination with at least one of phenylacetate and phenylbutyrate |
| HUE052140T2 (hu) | 2016-02-26 | 2021-04-28 | Debiopharm Int Sa | Diabéteszes lábfertõzések kezelésére szolgáló gyógyszer |
| IL270413B (en) | 2017-05-11 | 2022-08-01 | Ocera Therapeutics Inc | Processes of making l-ornithine phenylacetate |
| US10851125B2 (en) | 2017-08-01 | 2020-12-01 | Gilead Sciences, Inc. | Crystalline forms of ethyl ((S)-((((2R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl(-L-alaninate |
| CN113423390B (zh) | 2019-02-14 | 2023-05-23 | 德彪药业国际股份公司 | 阿法比星制剂及其制备方法 |
| EA202290048A1 (ru) | 2019-06-14 | 2022-03-10 | Дебиофарм Интернэшнл C.A. | Лекарственное средство и его применение для лечения бактериальных инфекций, связанных с биопленкой |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2698826A (en) * | 1951-02-13 | 1955-01-04 | Merco Centrifugal Co | Alcohol manufacturing process |
| US3437267A (en) * | 1966-03-24 | 1969-04-08 | Alfa Laval Ab | Centrifuge |
| JPH0244315B2 (ja) * | 1982-06-14 | 1990-10-03 | Microbial Chem Res Found | Supagarinn155hosufueetooyobisonoseizoho |
| US5723490A (en) | 1992-09-08 | 1998-03-03 | Vertex Pharmaceuticals Incorporated | THF-containing sulfonamide inhibitors of aspartyl protease |
| UA49803C2 (uk) * | 1994-06-03 | 2002-10-15 | Дж.Д. Сьорль Енд Ко | Спосіб лікування ретровірусних інфекцій |
| US6436989B1 (en) * | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| WO1999033793A2 (en) * | 1997-12-24 | 1999-07-08 | Vertex Pharmaceuticals Incorporated | Prodrugs of aspartyl protease inhibitors |
| WO1999033792A2 (en) | 1997-12-24 | 1999-07-08 | Vertex Pharmaceuticals Incorporated | Prodrugs os aspartyl protease inhibitors |
| GB9812189D0 (en) * | 1998-06-05 | 1998-08-05 | Glaxo Group Ltd | Methods and compositions for increasing penetration of HIV protease inhibitors |
| WO2000018384A2 (en) * | 1998-09-28 | 2000-04-06 | Glaxo Group Limited | Antiviral combinations comprising (s)-2-ethyl-7-fluoro-3-oxo-3,4-dihydro-2h-quinoxaline-1-carboxylic acid isopropyl ester and amprenavir |
| BR9914940A (pt) * | 1998-11-04 | 2001-07-10 | Upjohn Co | Método para aperfeiçoar a farmacocinética de tipranavir |
| CZ20002364A3 (cs) * | 1998-12-23 | 2000-11-15 | Vertex Pharmaceuticals Incorporated | Deriváty sulfonamidů a farmaceutický prostředek, který je obsahuje |
| GB9914821D0 (en) * | 1999-06-24 | 1999-08-25 | Glaxo Group Ltd | Compounds |
| AU777824B2 (en) * | 1999-11-24 | 2004-11-04 | Merck Sharp & Dohme Corp. | Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1- piperazinepentanamides as HIV protease inhibitors |
-
1998
- 1998-07-18 GB GBGB9815567.4A patent/GB9815567D0/en not_active Ceased
-
1999
- 1999-07-14 GC GCP1999203 patent/GC0000105A/xx active
- 1999-07-14 AR ARP990103446A patent/AR019388A1/es not_active Application Discontinuation
- 1999-07-14 DZ DZ990145A patent/DZ2845A1/xx active
- 1999-07-15 PT PT99934698T patent/PT1098898E/pt unknown
- 1999-07-15 MA MA25684A patent/MA26660A1/fr unknown
- 1999-07-15 EP EP02013136A patent/EP1240903A3/en not_active Withdrawn
- 1999-07-15 AP APAP/P/2001/002039A patent/AP2001002039A0/en unknown
- 1999-07-15 TR TR2001/00111T patent/TR200100111T2/xx unknown
- 1999-07-15 OA OA1200100016A patent/OA11706A/fr unknown
- 1999-07-15 PL PL99345620A patent/PL195736B1/pl unknown
- 1999-07-15 JP JP2000560139A patent/JP3437553B2/ja not_active Expired - Lifetime
- 1999-07-15 CZ CZ20010219A patent/CZ300447B6/cs not_active IP Right Cessation
- 1999-07-15 AU AU50379/99A patent/AU766056B2/en not_active Expired
- 1999-07-15 YU YU3401A patent/YU3401A/sh unknown
- 1999-07-15 US US09/744,051 patent/US6514953B1/en not_active Expired - Lifetime
- 1999-07-15 KR KR1020017000740A patent/KR100694721B1/ko not_active Expired - Lifetime
- 1999-07-15 JO JO19992114A patent/JO2114B1/en active
- 1999-07-15 EE EEP200100038A patent/EE200100038A/xx unknown
- 1999-07-15 WO PCT/EP1999/004991 patent/WO2000004033A1/en active IP Right Grant
- 1999-07-15 HU HU0103432A patent/HU229700B1/hu unknown
- 1999-07-15 GT GT199900111A patent/GT199900111A/es unknown
- 1999-07-15 PE PE1999000714A patent/PE20000869A1/es not_active Application Discontinuation
- 1999-07-15 BR BRPI9912156A patent/BRPI9912156B8/pt not_active IP Right Cessation
- 1999-07-15 TN TNTNSN99145A patent/TNSN99145A1/fr unknown
- 1999-07-15 MY MYPI99002983A patent/MY122323A/en unknown
- 1999-07-15 CA CA2337857A patent/CA2337857C/en not_active Expired - Lifetime
- 1999-07-15 EA EA200100053A patent/EA003191B1/ru not_active IP Right Cessation
- 1999-07-15 CO CO99044882A patent/CO5090836A1/es unknown
- 1999-07-15 ID IDW20010145A patent/ID28070A/id unknown
- 1999-07-15 NZ NZ509291A patent/NZ509291A/en not_active IP Right Cessation
- 1999-07-15 HR HR20010046A patent/HRP20010046A2/hr not_active Application Discontinuation
- 1999-07-15 SK SK76-2001A patent/SK285311B6/sk not_active IP Right Cessation
- 1999-07-15 DE DE69904600T patent/DE69904600T2/de not_active Expired - Lifetime
- 1999-07-15 IL IL14082499A patent/IL140824A/en not_active IP Right Cessation
- 1999-07-15 EP EP99934698A patent/EP1098898B1/en not_active Expired - Lifetime
- 1999-07-15 GE GEAP19995716A patent/GEP20033030B/en unknown
- 1999-07-15 SV SV1999000096A patent/SV1999000096A/es not_active Application Discontinuation
- 1999-07-15 AT AT99934698T patent/ATE229964T1/de active
- 1999-07-15 CN CNB998108383A patent/CN1188422C/zh not_active Expired - Lifetime
- 1999-07-15 ES ES99934698T patent/ES2189450T3/es not_active Expired - Lifetime
- 1999-07-15 DK DK99934698T patent/DK1098898T3/da active
- 1999-07-16 PA PA19998477801A patent/PA8477801A1/es unknown
- 1999-08-06 TW TW088113428A patent/TWI245770B/zh not_active IP Right Cessation
-
2001
- 2001-01-12 IS IS5808A patent/IS5808A/is unknown
- 2001-01-15 ZA ZA200100417A patent/ZA200100417B/en unknown
- 2001-01-17 NO NO20010282A patent/NO329676B1/no not_active IP Right Cessation
- 2001-02-14 BG BG105253A patent/BG105253A/xx unknown
-
2002
- 2002-11-25 US US10/303,366 patent/US20030096795A1/en not_active Abandoned
- 2002-11-25 US US10/303,213 patent/US20030100537A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO329676B1 (no) | Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat | |
| EA020489B1 (ru) | Модуляторы фармакокинетических свойств лекарственных средств | |
| RU2606951C1 (ru) | Дихлорацетаты замещенных N4-[2-(диметилфосфорил)фенил]-N2-(2-метокси-4-пиперидин-1-илфенил)-5-хлорпиримидин-2,4-диаминов в качестве модуляторов ALK и EGFR, предназначенных для лечения рака | |
| JP5869600B2 (ja) | アタザナビルを含む錠剤組成物 | |
| JP4774053B2 (ja) | Ｎ−ヒドロキシ−４−｛５−［４−（５−イソプロピル−２−メチル−１，３−チアゾール−４−イル）フェノキシ］ペントキシ｝メンズアミジン２メタンスルホン酸塩 | |
| EP3131878A1 (en) | Solid forms of a pharmaceutically active compound | |
| WO2001000635A2 (en) | Derivatives of (3s) tetrahydro-3-furanyl (1s,2r)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy)propylcarbamate | |
| KR101349752B1 (ko) | 정족수 감지 억제 활성 및 항균 활성을 갖는 항균용 조성물 | |
| MXPA01000617A (en) | Calcium (3s) tetrahydro-3- furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl](isobutyl) amino]-1-benzyl-2- (phosphonooxy) propylcarbamate | |
| HK1034261B (en) | Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino] -1-benzyl-2- (phosphonooxy) propylcarbamate | |
| DK200200115U3 (da) | Hidtil ukendte salte af 4-amino-1-hydroxybutyliden-1, 1-bisphosphonsyre, deres fremstilling og anvendelse | |
| JPH0352855A (ja) | アクリル酸塩、それらの製造方法、それらを含む薬剤組成物および医学におけるそれらの用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |