SK283939B6 - Spôsob výroby (3S)-tetrahydro-3-furyl-N-[(1S,2R)-3-(4-amino-N- izobutylbenzénsulfónamido)-1-benzyl-2-hydroxypropyl]karbamátu a medziprodukt - Google Patents
Spôsob výroby (3S)-tetrahydro-3-furyl-N-[(1S,2R)-3-(4-amino-N- izobutylbenzénsulfónamido)-1-benzyl-2-hydroxypropyl]karbamátu a medziprodukt Download PDFInfo
- Publication number
- SK283939B6 SK283939B6 SK1373-2000A SK13732000A SK283939B6 SK 283939 B6 SK283939 B6 SK 283939B6 SK 13732000 A SK13732000 A SK 13732000A SK 283939 B6 SK283939 B6 SK 283939B6
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- formula
- process according
- amino
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title abstract description 7
- 238000003786 synthesis reaction Methods 0.000 title abstract description 6
- 239000004030 hiv protease inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- -1 p-nitrophenylsulfonyl group Chemical group 0.000 claims description 28
- 125000006239 protecting group Chemical group 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 6
- XDPCNPCKDGQBAN-BYPYZUCNSA-N (3s)-oxolan-3-ol Chemical compound O[C@H]1CCOC1 XDPCNPCKDGQBAN-BYPYZUCNSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- BPRSPRGTVGSTKD-VQTJNVASSA-N rl02820 Chemical compound C([C@H](N)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(=CC=1)[N+]([O-])=O)C1=CC=CC=C1 BPRSPRGTVGSTKD-VQTJNVASSA-N 0.000 claims 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229940075894 denatured ethanol Drugs 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical group OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- VURIYNDSCXILBN-ZETCQYMHSA-N C1C[C@H](OC1)NC(=O)ON2C=CN=C2 Chemical compound C1C[C@H](OC1)NC(=O)ON2C=CN=C2 VURIYNDSCXILBN-ZETCQYMHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QIEVLZQUEZLVSY-UHFFFAOYSA-N n-(2-methylpropyl)-4-nitrobenzenesulfonamide Chemical compound CC(C)CNS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QIEVLZQUEZLVSY-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9805898.5A GB9805898D0 (en) | 1998-03-20 | 1998-03-20 | Process for the sythesis of hiv protease inhibitors |
| PCT/GB1999/000852 WO1999048885A1 (en) | 1998-03-20 | 1999-03-18 | Process for the synthesis of hiv protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK13732000A3 SK13732000A3 (sk) | 2001-08-06 |
| SK283939B6 true SK283939B6 (sk) | 2004-05-04 |
Family
ID=10828884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1373-2000A SK283939B6 (sk) | 1998-03-20 | 1999-03-18 | Spôsob výroby (3S)-tetrahydro-3-furyl-N-[(1S,2R)-3-(4-amino-N- izobutylbenzénsulfónamido)-1-benzyl-2-hydroxypropyl]karbamátu a medziprodukt |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6281367B1 (cs) |
| EP (1) | EP1066276B1 (cs) |
| JP (1) | JP3363439B2 (cs) |
| KR (1) | KR100555278B1 (cs) |
| CN (1) | CN1308319C (cs) |
| AP (1) | AP1226A (cs) |
| AT (1) | ATE242772T1 (cs) |
| AU (1) | AU751534B2 (cs) |
| BR (1) | BR9908970A (cs) |
| CA (1) | CA2324217C (cs) |
| CZ (1) | CZ299193B6 (cs) |
| DE (1) | DE69908761T2 (cs) |
| DK (1) | DK1066276T3 (cs) |
| EA (1) | EA003022B1 (cs) |
| EE (1) | EE04750B1 (cs) |
| ES (1) | ES2203090T3 (cs) |
| GB (1) | GB9805898D0 (cs) |
| HR (1) | HRP20000609B1 (cs) |
| HU (1) | HUP0105439A3 (cs) |
| ID (1) | ID26587A (cs) |
| IL (1) | IL138127A (cs) |
| IS (1) | IS2273B (cs) |
| NO (1) | NO317648B1 (cs) |
| NZ (1) | NZ506563A (cs) |
| PL (1) | PL201810B1 (cs) |
| PT (1) | PT1066276E (cs) |
| RS (1) | RS49954B (cs) |
| SK (1) | SK283939B6 (cs) |
| TR (1) | TR200002698T2 (cs) |
| WO (1) | WO1999048885A1 (cs) |
| ZA (1) | ZA200004482B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0656887B1 (en) | 1992-08-25 | 1998-10-28 | G.D. Searle & Co. | Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| EP2314564A3 (en) * | 1999-12-23 | 2012-04-04 | Ampac Fine Chemicals LLC | Improved preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines |
| US6548706B2 (en) * | 1999-12-23 | 2003-04-15 | Aerojet Fine Chemicals Llc | Preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl) -p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines |
| NZ536497A (en) | 2002-05-16 | 2006-08-31 | Tibotec Pharm Ltd | Pseudopolymorphic forms of a HIV protease inhibitor and their use as a medicament |
| BRPI0417272B8 (pt) * | 2003-12-23 | 2021-05-25 | Janssen R&D Ireland | processo para a preparação de (3r, 3as, 6ar)-hexahidrofuro [2,3-b] furan-3-il (1s, 2r)-3-[[(4-aminofenil) sulfonil] (isobutil) amino]-1-benzil-2-hidroxipropilcarbamato |
| ME01059B (me) | 2003-12-23 | 2012-10-20 | Janssen Sciences Ireland Uc | Proces za pripremanje (3r,3as,6ar)-heksahidrofuro [2,3-b] furan-3-il (1s,2r)-3-[[(4-aminofenil) sulfonil] (izobutil) amino]-1-benzil-2- hidroksipropilkarbamata |
| TWI482775B (zh) | 2008-09-01 | 2015-05-01 | Tibotec Pharm Ltd | 用於製備（３ｒ，３ａｓ，６ａｒ）－六氫呋喃并〔２，３－ｂ〕呋喃－３－基（１ｓ，２ｒ）－３－〔〔（４－胺基苯基）磺醯基〕（異丁基）胺基〕－１－苯甲基－２－羥基丙基胺基甲酸酯之方法 |
| EP3127542B1 (en) | 2010-01-27 | 2018-08-22 | VIIV Healthcare Company | Antiviral therapy |
| WO2012032389A2 (en) | 2010-09-10 | 2012-03-15 | Lupin Limited | Process for preparation of substantially pure fosamprenavir calcium and its intermediates |
| CN111233794A (zh) * | 2020-03-27 | 2020-06-05 | 江巨东 | 一种安普那韦的精制方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1071930A (zh) * | 1991-07-10 | 1993-05-12 | 伊莱利利公司 | 用作治疗艾滋病的人免疫缺陷病毒蛋白酶的抑制剂 |
| EP0656887B1 (en) * | 1992-08-25 | 1998-10-28 | G.D. Searle & Co. | Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US5723490A (en) * | 1992-09-08 | 1998-03-03 | Vertex Pharmaceuticals Incorporated | THF-containing sulfonamide inhibitors of aspartyl protease |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
-
1998
- 1998-03-20 GB GBGB9805898.5A patent/GB9805898D0/en not_active Ceased
-
1999
- 1999-03-18 KR KR1020007010359A patent/KR100555278B1/ko not_active Expired - Fee Related
- 1999-03-18 PL PL342602A patent/PL201810B1/pl not_active IP Right Cessation
- 1999-03-18 HR HR20000609A patent/HRP20000609B1/xx not_active IP Right Cessation
- 1999-03-18 ID IDW20001857A patent/ID26587A/id unknown
- 1999-03-18 NZ NZ506563A patent/NZ506563A/en unknown
- 1999-03-18 CZ CZ20003457A patent/CZ299193B6/cs not_active IP Right Cessation
- 1999-03-18 EA EA200000859A patent/EA003022B1/ru unknown
- 1999-03-18 PT PT99910543T patent/PT1066276E/pt unknown
- 1999-03-18 US US09/646,277 patent/US6281367B1/en not_active Expired - Lifetime
- 1999-03-18 EP EP99910543A patent/EP1066276B1/en not_active Expired - Lifetime
- 1999-03-18 BR BR9908970-0A patent/BR9908970A/pt not_active Application Discontinuation
- 1999-03-18 DE DE69908761T patent/DE69908761T2/de not_active Expired - Lifetime
- 1999-03-18 AU AU29475/99A patent/AU751534B2/en not_active Ceased
- 1999-03-18 DK DK99910543T patent/DK1066276T3/da active
- 1999-03-18 ES ES99910543T patent/ES2203090T3/es not_active Expired - Lifetime
- 1999-03-18 AT AT99910543T patent/ATE242772T1/de not_active IP Right Cessation
- 1999-03-18 EE EEP200000568A patent/EE04750B1/xx not_active IP Right Cessation
- 1999-03-18 CN CNB998042242A patent/CN1308319C/zh not_active Expired - Fee Related
- 1999-03-18 TR TR2000/02698T patent/TR200002698T2/xx unknown
- 1999-03-18 AP APAP/P/2000/001911A patent/AP1226A/en active
- 1999-03-18 HU HU0105439A patent/HUP0105439A3/hu unknown
- 1999-03-18 RS YUP-559/00A patent/RS49954B/sr unknown
- 1999-03-18 CA CA002324217A patent/CA2324217C/en not_active Expired - Fee Related
- 1999-03-18 JP JP2000537868A patent/JP3363439B2/ja not_active Expired - Lifetime
- 1999-03-18 SK SK1373-2000A patent/SK283939B6/sk not_active IP Right Cessation
- 1999-03-18 IL IL13812799A patent/IL138127A/xx not_active IP Right Cessation
- 1999-03-18 WO PCT/GB1999/000852 patent/WO1999048885A1/en active IP Right Grant
-
2000
- 2000-08-29 IS IS5605A patent/IS2273B/is unknown
- 2000-08-29 ZA ZA200004482A patent/ZA200004482B/en unknown
- 2000-09-19 NO NO20004664A patent/NO317648B1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2212326C (en) | O-carbamoyl-(d)-phenylalanilol compounds and process for preparing the same | |
| US20050080268A1 (en) | Process of preparing O-carbamoyl compounds in the presence of active amine group | |
| SK283939B6 (sk) | Spôsob výroby (3S)-tetrahydro-3-furyl-N-[(1S,2R)-3-(4-amino-N- izobutylbenzénsulfónamido)-1-benzyl-2-hydroxypropyl]karbamátu a medziprodukt | |
| US5925762A (en) | Practical synthesis of urea derivatives | |
| CN116813529A (zh) | 6-叔丁氧羰基-2-氨基-6-氮杂螺[3.4]辛烷的合成方法 | |
| CN112272665B (zh) | 制备立他司特的方法 | |
| RU2761167C1 (ru) | Способ получения картолина-2 | |
| CN111116420A (zh) | 一种对称脲类化合物的制备方法 | |
| JP2007521277A (ja) | 化合物の製造 | |
| MXPA00008925A (en) | Process for the synthesis of hiv protease inhibitors | |
| EA005399B1 (ru) | Способ получения производных дистамицина | |
| HK1032047B (en) | Process for the synthesis of hiv protease inhibitors | |
| JPH07291917A (ja) | アシルイソシアネート類の製造方法 | |
| Shi et al. | Reactions of 5‐methylene‐1, 3‐thiazolidine‐2‐thione and 5‐methylene‐2‐oxazolidinone with isocyanates catalyzed by bases | |
| US20020151718A1 (en) | Synthesis of pyrrole amides | |
| RU2775690C2 (ru) | Синтез транс-8-хлор-5-метил-1-[4-(пиридин-2-илокси)-циклогексил]-5,6-дигидро-4н-2,3,5,10в-тетраазабензо[e]азулена и его кристаллические формы | |
| KR960007530B1 (ko) | 설포닐우레아 유도체의 제조방법 | |
| JP2001151784A (ja) | １−アミノ−３−ハロ−２−（トリアルキルシロキシ）プロパンの製造法及び３−（トリアルキルシロキシ）アゼチジンの製造法 | |
| JPH04198178A (ja) | 光学活性を有する４―オキソクロマン―２―カルボン酸誘導体の製法 | |
| Kim et al. | Cyclization reaction of N-aroyl-N'-(2-hydroxyethyl) ureas: One-pot synthesis of 1-aroyl-2-imidazolidinones | |
| JPH09110817A (ja) | アシルイソシアネートの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100318 |