ZA200304687B - Method for carbamoylating alcohols. - Google Patents
Method for carbamoylating alcohols. Download PDFInfo
- Publication number
- ZA200304687B ZA200304687B ZA200304687A ZA200304687A ZA200304687B ZA 200304687 B ZA200304687 B ZA 200304687B ZA 200304687 A ZA200304687 A ZA 200304687A ZA 200304687 A ZA200304687 A ZA 200304687A ZA 200304687 B ZA200304687 B ZA 200304687B
- Authority
- ZA
- South Africa
- Prior art keywords
- alcohol
- sulfenyl
- acid
- cyanate
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 57
- 230000002252 carbamoylating effect Effects 0.000 title description 23
- 150000001298 alcohols Chemical class 0.000 title description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 67
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 60
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 30
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 28
- 239000011541 reaction mixture Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- -1 sulfenyl alcohol Chemical compound 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 230000021235 carbamoylation Effects 0.000 claims description 11
- 238000010791 quenching Methods 0.000 claims description 7
- 230000000171 quenching effect Effects 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000001913 cyanates Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- IGZGOSZOYWXTLI-UHFFFAOYSA-M cesium;cyanate Chemical compound [Cs+].[O-]C#N IGZGOSZOYWXTLI-UHFFFAOYSA-M 0.000 claims description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 57
- YQXCVAGCMNFUMQ-UHFFFAOYSA-N capravirine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)N=C(COC(N)=O)N1CC1=CC=NC=C1 YQXCVAGCMNFUMQ-UHFFFAOYSA-N 0.000 description 36
- 229950008230 capravirine Drugs 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 125000003158 alcohol group Chemical group 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000003443 antiviral agent Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000004615 ingredient Substances 0.000 description 3
- 238000006053 organic reaction Methods 0.000 description 3
- 150000003568 thioethers Chemical group 0.000 description 3
- AHQRTNSRMYQNSW-UHFFFAOYSA-N (3,5-dichlorophenyl) thiohypochlorite Chemical compound ClSC1=CC(Cl)=CC(Cl)=C1 AHQRTNSRMYQNSW-UHFFFAOYSA-N 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- WTPCCFHCHCMJIT-UHFFFAOYSA-N 1,2,5-oxathiazine Chemical compound O1SC=CN=C1 WTPCCFHCHCMJIT-UHFFFAOYSA-N 0.000 description 2
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000003341 Bronsted base Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JZTKNVMVUVSGJF-UHFFFAOYSA-N 1,2,3,5-oxatriazole Chemical compound C=1N=NON=1 JZTKNVMVUVSGJF-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- PPYNEJLGBMVWMC-UHFFFAOYSA-N 1,2,6-oxathiazine Chemical compound O1SC=CC=N1 PPYNEJLGBMVWMC-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FFJBRYXQVYFDEQ-UHFFFAOYSA-N 1,3,2-dioxazole Chemical compound N1OC=CO1 FFJBRYXQVYFDEQ-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- SMXOHNCXXITEJT-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1.C1=NC=NC=N1 SMXOHNCXXITEJT-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- JMQANWHMOHXBEA-UHFFFAOYSA-N 1,3-dichloro-5-[(3,5-dichlorophenyl)disulfanyl]benzene Chemical compound ClC1=CC(Cl)=CC(SSC=2C=C(Cl)C=C(Cl)C=2)=C1 JMQANWHMOHXBEA-UHFFFAOYSA-N 0.000 description 1
- ZWEGOVJVJZJDQJ-UHFFFAOYSA-N 1,4,2-dioxazole Chemical compound C1OC=NO1 ZWEGOVJVJZJDQJ-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
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- BZQYQHBLAIWZAC-UHFFFAOYSA-N 1h-2,3-benzoxazine Chemical compound C1=CC=C2CON=CC2=C1 BZQYQHBLAIWZAC-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
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- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- CGACGSHTSCXSSO-UHFFFAOYSA-N 2h-1,3-benzoxazine Chemical compound C1=CC=C2C=NCOC2=C1 CGACGSHTSCXSSO-UHFFFAOYSA-N 0.000 description 1
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 1
- ACVSHQGHCWUJFU-UHFFFAOYSA-N 2h-imidazole Chemical compound C1N=CC=N1 ACVSHQGHCWUJFU-UHFFFAOYSA-N 0.000 description 1
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- FLTFWLUOHKERMJ-UHFFFAOYSA-N pyrano[3,4-b]pyrrole Chemical compound C1=COC=C2N=CC=C21 FLTFWLUOHKERMJ-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26550201P | 2001-01-31 | 2001-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200304687B true ZA200304687B (en) | 2004-08-10 |
Family
ID=23010706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200304687A ZA200304687B (en) | 2001-01-31 | 2003-06-17 | Method for carbamoylating alcohols. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6613908B2 (cs) |
| EP (1) | EP1377568A1 (cs) |
| JP (1) | JP2004518687A (cs) |
| KR (1) | KR100567706B1 (cs) |
| CN (1) | CN1243748C (cs) |
| AR (1) | AR032419A1 (cs) |
| BR (1) | BR0206806A (cs) |
| CA (1) | CA2433364A1 (cs) |
| CZ (1) | CZ20032001A3 (cs) |
| HK (1) | HK1060573A1 (cs) |
| HU (1) | HUP0303028A3 (cs) |
| IL (1) | IL156363A0 (cs) |
| MX (1) | MXPA03005403A (cs) |
| PL (1) | PL363321A1 (cs) |
| RU (1) | RU2256657C2 (cs) |
| TW (1) | TWI228507B (cs) |
| WO (1) | WO2002060893A1 (cs) |
| YU (1) | YU52303A (cs) |
| ZA (1) | ZA200304687B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1628685T3 (da) | 2003-04-25 | 2011-03-21 | Gilead Sciences Inc | Antivirale phosphonatanaloge |
| US7579332B2 (en) * | 2003-07-30 | 2009-08-25 | Gilead Sciences, Inc. | Nucleobase phosphonate analogs for antiviral treatment |
| WO2005016912A1 (en) * | 2003-08-19 | 2005-02-24 | Pfizer Inc. | An efficient microbial preparation of capravirine metabolites m4 and m5 |
| US20050080268A1 (en) * | 2003-10-08 | 2005-04-14 | Yong-Moon Choi | Process of preparing O-carbamoyl compounds in the presence of active amine group |
| AR050174A1 (es) * | 2004-07-16 | 2006-10-04 | Gilead Sciences Inc | Derivados de fosfonatos con actividad antiviral. composiciones farmaceuticas |
| HUE043207T2 (hu) | 2004-07-27 | 2019-08-28 | Gilead Sciences Inc | HIV-gátló vegyületek foszfonát analógjai |
| TWI389908B (zh) * | 2005-07-14 | 2013-03-21 | Gilead Sciences Inc | 抗病毒化合物類 |
| TW200738742A (en) * | 2005-07-14 | 2007-10-16 | Gilead Sciences Inc | Antiviral compounds |
| CA2616314A1 (en) * | 2005-07-27 | 2007-02-01 | Gilead Sciences, Inc. | Antiviral phosphonate conjugates for inhibition of hiv |
| WO2008005542A2 (en) * | 2006-07-07 | 2008-01-10 | Gilead Sciences, Inc., | Antiviral phosphinate compounds |
| US20100093667A1 (en) | 2008-07-08 | 2010-04-15 | Gilead Sciences, Inc. | Salts of hiv inhibitor compounds |
| US8810796B2 (en) | 2009-04-21 | 2014-08-19 | Michigan Aerospace Corporation | Light processing system and method |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2611695A1 (de) * | 1976-03-19 | 1977-09-29 | Hoechst Ag | Herbizide mittel |
| BR9509024A (pt) | 1994-09-26 | 1997-09-30 | Shionogi & Co | Derivados de imidazol |
-
2002
- 2002-01-11 EP EP02737611A patent/EP1377568A1/en not_active Withdrawn
- 2002-01-11 JP JP2002561042A patent/JP2004518687A/ja active Pending
- 2002-01-11 RU RU2003123791/04A patent/RU2256657C2/ru not_active IP Right Cessation
- 2002-01-11 CN CNB028042816A patent/CN1243748C/zh not_active Expired - Fee Related
- 2002-01-11 PL PL02363321A patent/PL363321A1/xx not_active Application Discontinuation
- 2002-01-11 WO PCT/IB2002/000082 patent/WO2002060893A1/en not_active Application Discontinuation
- 2002-01-11 CZ CZ20032001A patent/CZ20032001A3/cs unknown
- 2002-01-11 MX MXPA03005403A patent/MXPA03005403A/es not_active Application Discontinuation
- 2002-01-11 HU HU0303028A patent/HUP0303028A3/hu unknown
- 2002-01-11 IL IL15636302A patent/IL156363A0/xx unknown
- 2002-01-11 YU YU52303A patent/YU52303A/sh unknown
- 2002-01-11 CA CA002433364A patent/CA2433364A1/en not_active Abandoned
- 2002-01-11 KR KR1020037010036A patent/KR100567706B1/ko not_active IP Right Cessation
- 2002-01-11 BR BR0206806-0A patent/BR0206806A/pt not_active IP Right Cessation
- 2002-01-25 TW TW091101284A patent/TWI228507B/zh not_active IP Right Cessation
- 2002-01-25 US US10/056,268 patent/US6613908B2/en not_active Expired - Fee Related
- 2002-01-29 AR ARP020100312A patent/AR032419A1/es unknown
-
2003
- 2003-06-17 ZA ZA200304687A patent/ZA200304687B/en unknown
-
2004
- 2004-05-21 HK HK04103611A patent/HK1060573A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0303028A2 (hu) | 2003-12-29 |
| JP2004518687A (ja) | 2004-06-24 |
| KR20030069227A (ko) | 2003-08-25 |
| RU2256657C2 (ru) | 2005-07-20 |
| RU2003123791A (ru) | 2005-02-27 |
| IL156363A0 (en) | 2004-01-04 |
| WO2002060893A1 (en) | 2002-08-08 |
| CA2433364A1 (en) | 2002-08-08 |
| YU52303A (sh) | 2006-05-25 |
| CN1489584A (zh) | 2004-04-14 |
| BR0206806A (pt) | 2004-02-03 |
| MXPA03005403A (es) | 2003-09-25 |
| CN1243748C (zh) | 2006-03-01 |
| KR100567706B1 (ko) | 2006-04-05 |
| HK1060573A1 (en) | 2004-08-13 |
| US20020103378A1 (en) | 2002-08-01 |
| US6613908B2 (en) | 2003-09-02 |
| AR032419A1 (es) | 2003-11-05 |
| EP1377568A1 (en) | 2004-01-07 |
| PL363321A1 (en) | 2004-11-15 |
| HUP0303028A3 (en) | 2005-10-28 |
| CZ20032001A3 (en) | 2004-06-16 |
| TWI228507B (en) | 2005-03-01 |
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