ZA200304687B - Method for carbamoylating alcohols. - Google Patents

Method for carbamoylating alcohols. Download PDF

Info

Publication number: ZA200304687B
Authority: ZA; South Africa
Prior art keywords: alcohol; sulfenyl; acid; cyanate; reaction
Prior art date: 2001-01-31

Application number

ZA200304687A

Other languages

English (en)

Inventor

James Edward Ellis

Original Assignee

Warner Lambert Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-01-31

Filing date

2003-06-17

Publication date

2004-08-10

2003-06-17 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2004-08-10 Publication of ZA200304687B publication Critical patent/ZA200304687B/en

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
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
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
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
IEMAOEFPZAIMCN-UHFFFAOYSA-N 1H-pyrazole Chemical compound C=1C=NNC=1.C=1C=NNC=1 IEMAOEFPZAIMCN-UHFFFAOYSA-N 0.000 description 1
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
JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 1
HPYLZSUEFFQHRS-UHFFFAOYSA-N 2h-1,2,4-oxadiazine Chemical compound N1OC=CN=C1 HPYLZSUEFFQHRS-UHFFFAOYSA-N 0.000 description 1
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
VXIKDBJPBRMXBP-UHFFFAOYSA-N 3H-pyrrole Chemical compound C1C=CN=C1 VXIKDBJPBRMXBP-UHFFFAOYSA-N 0.000 description 1
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BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
QDUHQAQMOAHLRW-UHFFFAOYSA-N 4h-1,4-benzoxazine Chemical compound C1=CC=C2NC=COC2=C1 QDUHQAQMOAHLRW-UHFFFAOYSA-N 0.000 description 1
UOSQFVCDJBZRKS-UHFFFAOYSA-N 4h-1,4-oxazine Chemical compound N1C=COC=C1 UOSQFVCDJBZRKS-UHFFFAOYSA-N 0.000 description 1
XAZNOOMRYLFDQO-UHFFFAOYSA-N 4h-3,1-benzoxazine Chemical compound C1=CC=C2COC=NC2=C1 XAZNOOMRYLFDQO-UHFFFAOYSA-N 0.000 description 1
BMRPOOWUTVUBRI-UHFFFAOYSA-N 4h-oxazine Chemical compound C1C=CON=C1 BMRPOOWUTVUBRI-UHFFFAOYSA-N 0.000 description 1
GMLMFZXBPRIXPK-UHFFFAOYSA-N 6h-1,3-oxazine Chemical compound C1OC=NC=C1 GMLMFZXBPRIXPK-UHFFFAOYSA-N 0.000 description 1
QFPDHKBNCJAOKJ-UHFFFAOYSA-N 6h-oxazine Chemical compound C1ON=CC=C1 QFPDHKBNCJAOKJ-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
OGVGYIYHTNXSRB-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.C(C1=CC=CC=C1)OCC=1N(C=CN1)CC1(CC=NC=C1)C(C)C Chemical compound C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.C(C1=CC=CC=C1)OCC=1N(C=CN1)CC1(CC=NC=C1)C(C)C OGVGYIYHTNXSRB-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
229950000178 cyclopentobarbital Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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
239000012044 organic layer Substances 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
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)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)

ZA200304687A 2001-01-31 2003-06-17 Method for carbamoylating alcohols. ZA200304687B (en)

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

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ID=23010706

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Application Number	Title	Priority Date	Filing Date
ZA200304687A ZA200304687B (en)	2001-01-31	2003-06-17	Method for carbamoylating alcohols.

Country Status (18)

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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)
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)

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PL1628685T3 (pl)	2003-04-25	2011-05-31	Gilead Sciences Inc	Przeciwwirusowe analogi fosfonianowe
EP1656387A2 (en) *	2003-07-30	2006-05-17	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
DK1778702T3 (da) *	2004-07-16	2011-10-17	Gilead Sciences Inc	Antivirale forbindelser
EP1778251B1 (en)	2004-07-27	2011-04-13	Gilead Sciences, Inc.	Nucleoside phosphonate conjugates as anti hiv agents
TW200738742A (en) *	2005-07-14	2007-10-16	Gilead Sciences Inc	Antiviral compounds
TWI389908B (zh) *	2005-07-14	2013-03-21	Gilead Sciences Inc	抗病毒化合物類
US20080076740A1 (en) *	2005-07-27	2008-03-27	Gilead Sciences, Inc.	Antiviral compounds
WO2008005542A2 (en) *	2006-07-07	2008-01-10	Gilead Sciences, Inc.,	Antiviral phosphinate compounds
AU2009268681B2 (en) *	2008-07-08	2014-10-02	Gilead Sciences, Inc.	Salts of HIV inhibitor compounds
US8810796B2 (en)	2009-04-21	2014-08-19	Michigan Aerospace Corporation	Light processing system and method
EP3661937B1 (en)	2017-08-01	2021-07-28	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 (gs-9131) for treating viral infections

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DE2611695A1 (de) *	1976-03-19	1977-09-29	Hoechst Ag	Herbizide mittel
DE69532245T2 (de)	1994-09-26	2004-09-16	Shionogi & Co., Ltd.	Imidazolderivat

2002
- 2002-01-11 KR KR1020037010036A patent/KR100567706B1/ko not_active Expired - Fee Related
- 2002-01-11 PL PL02363321A patent/PL363321A1/xx not_active Application Discontinuation
- 2002-01-11 YU YU52303A patent/YU52303A/sh unknown
- 2002-01-11 EP EP02737611A patent/EP1377568A1/en not_active Withdrawn
- 2002-01-11 BR BR0206806-0A patent/BR0206806A/pt not_active IP Right Cessation
- 2002-01-11 MX MXPA03005403A patent/MXPA03005403A/es not_active Application Discontinuation
- 2002-01-11 WO PCT/IB2002/000082 patent/WO2002060893A1/en not_active Ceased
- 2002-01-11 RU RU2003123791/04A patent/RU2256657C2/ru not_active IP Right Cessation
- 2002-01-11 JP JP2002561042A patent/JP2004518687A/ja active Pending
- 2002-01-11 CZ CZ20032001A patent/CZ20032001A3/cs unknown
- 2002-01-11 CN CNB028042816A patent/CN1243748C/zh not_active Expired - Fee Related
- 2002-01-11 CA CA002433364A patent/CA2433364A1/en not_active Abandoned
- 2002-01-11 IL IL15636302A patent/IL156363A0/xx unknown
- 2002-01-11 HU HU0303028A patent/HUP0303028A3/hu unknown
- 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

Also Published As

Publication number	Publication date
HUP0303028A3 (en)	2005-10-28
CN1243748C (zh)	2006-03-01
RU2003123791A (ru)	2005-02-27
CN1489584A (zh)	2004-04-14
PL363321A1 (en)	2004-11-15
CZ20032001A3 (en)	2004-06-16
IL156363A0 (en)	2004-01-04
HUP0303028A2 (hu)	2003-12-29
BR0206806A (pt)	2004-02-03
US6613908B2 (en)	2003-09-02
US20020103378A1 (en)	2002-08-01
AR032419A1 (es)	2003-11-05
KR100567706B1 (ko)	2006-04-05
WO2002060893A1 (en)	2002-08-08
KR20030069227A (ko)	2003-08-25
RU2256657C2 (ru)	2005-07-20
MXPA03005403A (es)	2003-09-25
HK1060573A1 (en)	2004-08-13
YU52303A (sh)	2006-05-25
EP1377568A1 (en)	2004-01-07
CA2433364A1 (en)	2002-08-08
TWI228507B (en)	2005-03-01
JP2004518687A (ja)	2004-06-24

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AU2002216333A1 (en)	2002-08-12	Method for carbamoylating alcohols
JPS59104364A (ja)	1984-06-16	新規ピリミジン誘導体およびその製造法
JPH10175957A (ja)	1998-06-30	１−エチル−５−ヒドロキシピラゾールの製法
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SU843742A3 (ru)	1981-06-30	Способ получени триацетонамина
JPS63264448A (ja)	1988-11-01	新規β−ケトニトリル
KR830002349B1 (ko)	1983-10-24	4-(5)-하이드록시메틸 5(4)-저급알킬이미다졸류의 제조방법
JPS6127961A (ja)	1986-02-07	Ｎ−置換フタルイミドの製造方法
JPH01249739A (ja)	1989-10-05	オルトー脂肪族オキシフェノール誘導体の製造方法
RU2161152C2 (ru)	2000-12-27	Способ получения 2-тиобарбитуровой кислоты
CN1315781C (zh)	2007-05-16	制备4－氨基－1－萘酚醚类化合物的方法
US4189578A (en)	1980-02-19	3-(o-Hydroxyphenyl)-5-formylhydrazino-Δ2 -pyrazolines
JPS61186359A (ja)	1986-08-20	ホルムアミド誘導体の製造方法
JPH0374218B2 (cs)	1991-11-26
JPS6322545A (ja)	1988-01-30	クロロアルキルアミン塩酸塩類の製造方法