NO318697B1 - Fremgangsmate for fremstilling av aminoalkoholderivater - Google Patents
Fremgangsmate for fremstilling av aminoalkoholderivater Download PDFInfo
- Publication number
- NO318697B1 NO318697B1 NO19985511A NO985511A NO318697B1 NO 318697 B1 NO318697 B1 NO 318697B1 NO 19985511 A NO19985511 A NO 19985511A NO 985511 A NO985511 A NO 985511A NO 318697 B1 NO318697 B1 NO 318697B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- approx
- hept
- cyclopentene
- azabicyclo
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000001414 amino alcohols Chemical class 0.000 title claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 229910052987 metal hydride Inorganic materials 0.000 claims description 11
- 150000004681 metal hydrides Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- DDUFYKNOXPZZIW-UHFFFAOYSA-N 3-azabicyclo[2.2.1]hept-5-en-2-one Chemical compound C1C2C(=O)NC1C=C2 DDUFYKNOXPZZIW-UHFFFAOYSA-N 0.000 abstract description 23
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract description 4
- OSFRHUVOPNVUGL-NKWVEPMBSA-N n-[2-amino-4-chloro-6-[[(1s,4r)-4-(hydroxymethyl)cyclopent-2-en-1-yl]amino]pyrimidin-5-yl]formamide Chemical compound NC1=NC(Cl)=C(NC=O)C(N[C@@H]2C=C[C@H](CO)C2)=N1 OSFRHUVOPNVUGL-NKWVEPMBSA-N 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- JPZOAVGMSDSWSW-UHFFFAOYSA-N 4,6-dichloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(Cl)=N1 JPZOAVGMSDSWSW-UHFFFAOYSA-N 0.000 abstract 1
- IHEDZPMXLKYPSA-NKWVEPMBSA-N [(1r,4s)-4-(2-amino-6-chloropurin-9-yl)cyclopent-2-en-1-yl]methanol Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1[C@H]1C[C@@H](CO)C=C1 IHEDZPMXLKYPSA-NKWVEPMBSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- -1 lithium aluminum hydride Chemical compound 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000012448 Lithium borohydride Substances 0.000 description 8
- UXKZFJDNFBNQHE-RITPCOANSA-N [(1s,4r)-4-aminocyclopent-2-en-1-yl]methanol Chemical compound N[C@@H]1C[C@H](CO)C=C1 UXKZFJDNFBNQHE-RITPCOANSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- IHLRGGLJGGTPCY-HWKANZROSA-N (e)-hept-5-en-3-one Chemical compound CCC(=O)C\C=C\C IHLRGGLJGGTPCY-HWKANZROSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- UXKZFJDNFBNQHE-UHFFFAOYSA-N (4-aminocyclopent-2-en-1-yl)methanol Chemical compound NC1CC(CO)C=C1 UXKZFJDNFBNQHE-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Chemical compound [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- XSSYCIGJYCVRRK-RQJHMYQMSA-N (-)-carbovir Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1C[C@H](CO)C=C1 XSSYCIGJYCVRRK-RQJHMYQMSA-N 0.000 description 1
- VTCHZFWYUPZZKL-CRCLSJGQSA-N (1r,4s)-4-azaniumylcyclopent-2-ene-1-carboxylate Chemical compound N[C@H]1C[C@@H](C(O)=O)C=C1 VTCHZFWYUPZZKL-CRCLSJGQSA-N 0.000 description 1
- WTXGYGWMPUGBAL-SQOUGZDYSA-N (3r,4s,5r,6r)-3,4,5,6-tetrahydroxyoxepan-2-one Chemical compound O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@@H]1O WTXGYGWMPUGBAL-SQOUGZDYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 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
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 1
- 229930195711 D-Serine Natural products 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000589771 Ralstonia solanacearum Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- UXKZFJDNFBNQHE-NTSWFWBYSA-N [(1r,4s)-4-aminocyclopent-2-en-1-yl]methanol Chemical class N[C@H]1C[C@@H](CO)C=C1 UXKZFJDNFBNQHE-NTSWFWBYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- RWASOQSEFLDYLC-UHFFFAOYSA-N beryllium dihydride Chemical compound [BeH2] RWASOQSEFLDYLC-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910012375 magnesium hydride Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- NQIZWJGHIYDHRL-SFYZADRCSA-N tert-butyl (1s,4r)-2-oxo-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate Chemical compound C1[C@@]2([H])C=C[C@]1([H])N(C(=O)OC(C)(C)C)C2=O NQIZWJGHIYDHRL-SFYZADRCSA-N 0.000 description 1
- WFRBDWRZVBPBDO-UHFFFAOYSA-N tert-hexyl alcohol Natural products CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/23—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH273997 | 1997-11-27 | ||
CH278197 | 1997-12-03 | ||
CH13398 | 1998-01-21 | ||
CH72398 | 1998-03-27 | ||
EP98118895 | 1998-10-07 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO985511D0 NO985511D0 (no) | 1998-11-26 |
NO985511L NO985511L (no) | 1999-05-28 |
NO318697B1 true NO318697B1 (no) | 2005-04-25 |
Family
ID=27508776
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19985511A NO318697B1 (no) | 1997-11-27 | 1998-11-26 | Fremgangsmate for fremstilling av aminoalkoholderivater |
NO20044369A NO327575B1 (no) | 1997-11-27 | 2004-10-14 | Fremgangsmate for fremstilling av optisk aktive (1S,4R)- eller (1R, 4S)-1-amino-4-(hydroksymetyl)-2-cyklopentener eller deres salter og/eller av (1S,4R)- eller (1R, 4S)-1-amino-4-(hydroksymetyl)-2-cyklopentenderivater eller deres salter |
NO20044368A NO326251B1 (no) | 1997-11-27 | 2004-10-14 | Fremgangsmate for fremstilling av aminoalkoholderivater |
NO20044370A NO20044370L (no) | 1997-11-27 | 2004-10-14 | Fremgangsmate for fremstilling av et optisk aktivt purinderivat |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20044369A NO327575B1 (no) | 1997-11-27 | 2004-10-14 | Fremgangsmate for fremstilling av optisk aktive (1S,4R)- eller (1R, 4S)-1-amino-4-(hydroksymetyl)-2-cyklopentener eller deres salter og/eller av (1S,4R)- eller (1R, 4S)-1-amino-4-(hydroksymetyl)-2-cyklopentenderivater eller deres salter |
NO20044368A NO326251B1 (no) | 1997-11-27 | 2004-10-14 | Fremgangsmate for fremstilling av aminoalkoholderivater |
NO20044370A NO20044370L (no) | 1997-11-27 | 2004-10-14 | Fremgangsmate for fremstilling av et optisk aktivt purinderivat |
Country Status (18)
Country | Link |
---|---|
US (5) | US6723868B1 (sk) |
EP (5) | EP1418170B1 (sk) |
JP (4) | JP4372873B2 (sk) |
KR (4) | KR100615370B1 (sk) |
CN (4) | CN1323057C (sk) |
AT (4) | ATE478073T1 (sk) |
CA (4) | CA2591571A1 (sk) |
CZ (4) | CZ298102B6 (sk) |
DE (4) | DE59810751D1 (sk) |
DK (3) | DK0926131T3 (sk) |
ES (3) | ES2312906T3 (sk) |
HK (2) | HK1070103A1 (sk) |
HU (3) | HU226473B1 (sk) |
IL (5) | IL160787A (sk) |
NO (4) | NO318697B1 (sk) |
PL (2) | PL207859B1 (sk) |
PT (4) | PT1508565E (sk) |
SK (4) | SK284594B6 (sk) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT1141374E (pt) * | 1998-12-23 | 2004-03-31 | Lonza Ag | Processo para a producao de derivados de 1-amino-4-(hidroximetil)ciclopent-2-eno opticamente activos |
US8042740B2 (en) * | 2000-11-24 | 2011-10-25 | Metrologic Instruments, Inc. | Method of reading bar code symbols on objects at a point-of-sale station by passing said objects through a complex of stationary coplanar illumination and imaging planes projected into a 3D imaging volume |
IL160527A0 (en) * | 2001-09-25 | 2004-07-25 | Hoffmann La Roche | Enzymatic process for the preparation of substituted 2-amino-3 (2-aminophenylsulfanyl)-propionic acid |
KR100684772B1 (ko) | 2004-12-08 | 2007-02-22 | 주식회사농심 | 찹쌀을 이용한 푸딩 촉감의 식품 및 그의 제조 방법. |
US8805134B1 (en) | 2012-02-17 | 2014-08-12 | Soraa Laser Diode, Inc. | Methods and apparatus for photonic integration in non-polar and semi-polar oriented wave-guided optical devices |
US9250044B1 (en) | 2009-05-29 | 2016-02-02 | Soraa Laser Diode, Inc. | Gallium and nitrogen containing laser diode dazzling devices and methods of use |
US9039655B2 (en) | 2009-11-06 | 2015-05-26 | Crisi Medical Systems, Inc. | Medication injection site and data collection system |
CN102603652A (zh) * | 2011-12-27 | 2012-07-25 | 河南师范大学 | 5-甲酰基嘧啶碳环核苷及制备方法 |
CN102719512B (zh) * | 2012-06-21 | 2014-06-11 | 浙江工业大学 | 一种r-2-(4-羟基苯氧基)丙酸酯的制备方法 |
CN104098478B (zh) * | 2013-04-08 | 2017-05-17 | 安徽贝克联合制药有限公司 | 一种氨基醇的拆分方法 |
US10385006B2 (en) * | 2014-10-27 | 2019-08-20 | Granules India Limited | Process for the preparation of amino alcohol derivatives or salts thereof |
CN104974051A (zh) * | 2015-06-30 | 2015-10-14 | 苏州开元民生科技股份有限公司 | (1S,4R)-cis-4-氨基-2-环戊烯-1-甲醇盐酸盐的合成方法 |
CN106220515A (zh) * | 2016-08-12 | 2016-12-14 | 郸城巨鑫生物科技有限公司 | 一种(1r,4s)‑1‑氨基‑4‑羟甲基‑2‑环戊烯盐酸盐的合成方法 |
EP3523280A1 (en) * | 2016-10-06 | 2019-08-14 | Janssen Pharmaceutica NV | Processes and intermediates for preparing a btk inhibitor |
US11239637B2 (en) | 2018-12-21 | 2022-02-01 | Kyocera Sld Laser, Inc. | Fiber delivered laser induced white light system |
US11421843B2 (en) | 2018-12-21 | 2022-08-23 | Kyocera Sld Laser, Inc. | Fiber-delivered laser-induced dynamic light system |
CN109735582B (zh) * | 2018-12-24 | 2022-06-21 | 浙江工业大学 | 一种脂肪酶催化在线合成环己醇类β-氨基醇衍生物的方法 |
US12000552B2 (en) | 2019-01-18 | 2024-06-04 | Kyocera Sld Laser, Inc. | Laser-based fiber-coupled white light system for a vehicle |
US11884202B2 (en) | 2019-01-18 | 2024-01-30 | Kyocera Sld Laser, Inc. | Laser-based fiber-coupled white light system |
CN116730856B (zh) * | 2023-06-19 | 2024-06-07 | 浙江竹子制药有限公司 | 一种氨甲环酸的合成方法 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2534533A (en) | 1945-11-05 | 1950-12-19 | Hermann I Schlesinger | Methods of preparing alkali metal borohydrides |
DE947702C (de) | 1954-07-16 | 1956-08-23 | Metallgesellschaft Ag | Verfahren zur Herstellung borhaltiger Metallhydride |
US4138562A (en) | 1977-02-09 | 1979-02-06 | The Regents Of The University Of Minnesota | Adenosine deaminase resistant antiviral purine nucleosides and method of preparation |
US4268672A (en) * | 1977-02-09 | 1981-05-19 | The Regents Of The University Of Minnesota | Adenosine deaminase resistant antiviral purine nucleosides and method of preparation |
US4916224A (en) * | 1988-01-20 | 1990-04-10 | Regents Of The University Of Minnesota | Dideoxycarbocyclic nucleosides |
GB8815265D0 (en) * | 1988-06-27 | 1988-08-03 | Wellcome Found | Therapeutic nucleosides |
AU626314B2 (en) * | 1988-09-09 | 1992-07-30 | Ferag Ag | Method and means for tabloid further processing |
MY104575A (en) * | 1989-12-22 | 1994-04-30 | The Wellcome Foundation Ltd | Therapeutic nucleosides. |
JPH0484896A (ja) * | 1990-07-26 | 1992-03-18 | Kyowa Hakko Kogyo Co Ltd | 光学活性なイソインドリン―1―オン誘導体の製造法 |
US5200527A (en) | 1991-04-08 | 1993-04-06 | Lonza Ltd. | Process for the production of 2-azabicyclo [2.2.1] hept-5-en-3-one |
FR2676042B1 (fr) | 1991-05-02 | 1993-07-23 | Commissariat Energie Atomique | Procede de preparation d'un borohydrure de metal alcalin tel que le borohydrure de lithium. |
GB9204015D0 (en) | 1992-02-25 | 1992-04-08 | Wellcome Found | Therapeutic nucleosides |
GB9402161D0 (en) * | 1994-02-04 | 1994-03-30 | Wellcome Found | Chloropyrimidine intermediates |
GB9417249D0 (en) * | 1994-08-26 | 1994-10-19 | Wellcome Found | A novel salt |
JPH09124564A (ja) * | 1995-11-06 | 1997-05-13 | Nikko Rika Kk | 光学活性体混合物ならびにその製造方法 |
AU1271897A (en) * | 1995-11-16 | 1997-06-05 | G.D. Searle & Co. | N-protected/n-substituted-beta-amino hydroxy sulfonates |
IL127235A (en) * | 1996-05-30 | 2003-04-10 | Lonza Ag | Process for the preparation of amino alcohols and derivatives thereof |
SK285229B6 (sk) * | 1997-05-13 | 2006-09-07 | Lonza Ag | Spôsob výroby derivátov (1R,4S)- alebo (1S,4R)-1-amino-4- (hydroxymetyl)-2-cyklopenténu a enantioméru (1R,4S)-N-butyryl-1- amino-4-(hydroxymetyl)-2-cyklopenténu |
GB9721780D0 (en) * | 1997-10-14 | 1997-12-10 | Glaxo Group Ltd | Process for the synthesis of chloropurine intermediates |
-
1998
- 1998-11-23 CZ CZ0381798A patent/CZ298102B6/cs not_active IP Right Cessation
- 1998-11-23 CZ CZ20070123A patent/CZ298144B6/cs not_active IP Right Cessation
- 1998-11-23 SK SK401-2004A patent/SK284594B6/sk not_active IP Right Cessation
- 1998-11-23 SK SK402-2004A patent/SK284595B6/sk not_active IP Right Cessation
- 1998-11-23 SK SK403-2004A patent/SK284596B6/sk not_active IP Right Cessation
- 1998-11-23 SK SK1615-98A patent/SK284416B6/sk not_active IP Right Cessation
- 1998-11-23 CZ CZ20070124A patent/CZ299083B6/cs not_active IP Right Cessation
- 1998-11-23 CZ CZ20070122A patent/CZ298913B6/cs not_active IP Right Cessation
- 1998-11-24 EP EP04002913A patent/EP1418170B1/de not_active Expired - Lifetime
- 1998-11-24 PT PT04027540T patent/PT1508565E/pt unknown
- 1998-11-24 US US09/198,427 patent/US6723868B1/en not_active Expired - Fee Related
- 1998-11-24 EP EP98122293A patent/EP0926131B1/de not_active Expired - Lifetime
- 1998-11-24 KR KR1019980050483A patent/KR100615370B1/ko not_active IP Right Cessation
- 1998-11-24 DE DE59810751T patent/DE59810751D1/de not_active Expired - Lifetime
- 1998-11-24 AT AT06002571T patent/ATE478073T1/de active
- 1998-11-24 DE DE59814466T patent/DE59814466D1/de not_active Expired - Lifetime
- 1998-11-24 EP EP08161021A patent/EP1982985A3/de not_active Withdrawn
- 1998-11-24 AT AT98122293T patent/ATE259345T1/de active
- 1998-11-24 PT PT98122293T patent/PT926131E/pt unknown
- 1998-11-24 AT AT04002913T patent/ATE328863T1/de active
- 1998-11-24 PT PT04002913T patent/PT1418170E/pt unknown
- 1998-11-24 ES ES04027540T patent/ES2312906T3/es not_active Expired - Lifetime
- 1998-11-24 AT AT04027540T patent/ATE404689T1/de active
- 1998-11-24 DK DK98122293T patent/DK0926131T3/da active
- 1998-11-24 DE DE59814270T patent/DE59814270D1/de not_active Expired - Lifetime
- 1998-11-24 DK DK06002571.5T patent/DK1657243T3/da active
- 1998-11-24 ES ES98122293T patent/ES2215264T3/es not_active Expired - Lifetime
- 1998-11-24 ES ES04002913T patent/ES2270192T3/es not_active Expired - Lifetime
- 1998-11-24 EP EP04027540A patent/EP1508565B1/de not_active Expired - Lifetime
- 1998-11-24 EP EP06002571A patent/EP1657243B1/de not_active Expired - Lifetime
- 1998-11-24 DE DE59813589T patent/DE59813589D1/de not_active Expired - Lifetime
- 1998-11-24 DK DK04002913T patent/DK1418170T3/da active
- 1998-11-24 PT PT06002571T patent/PT1657243E/pt unknown
- 1998-11-25 CA CA002591571A patent/CA2591571A1/en not_active Abandoned
- 1998-11-25 CA CA002254693A patent/CA2254693C/en not_active Expired - Fee Related
- 1998-11-25 CA CA2591818A patent/CA2591818C/en not_active Expired - Fee Related
- 1998-11-25 CA CA2591566A patent/CA2591566C/en not_active Expired - Fee Related
- 1998-11-26 IL IL160787A patent/IL160787A/en not_active IP Right Cessation
- 1998-11-26 IL IL12727798A patent/IL127277A/en not_active IP Right Cessation
- 1998-11-26 IL IL14262298A patent/IL142622A/en not_active IP Right Cessation
- 1998-11-26 IL IL14262398A patent/IL142623A/en not_active IP Right Cessation
- 1998-11-26 NO NO19985511A patent/NO318697B1/no not_active IP Right Cessation
- 1998-11-27 HU HU0700623A patent/HU226473B1/hu not_active IP Right Cessation
- 1998-11-27 PL PL380973A patent/PL207859B1/pl not_active IP Right Cessation
- 1998-11-27 JP JP33743798A patent/JP4372873B2/ja not_active Expired - Fee Related
- 1998-11-27 HU HU0700624A patent/HU226475B1/hu not_active IP Right Cessation
- 1998-11-27 CN CNB2004100435565A patent/CN1323057C/zh not_active Expired - Fee Related
- 1998-11-27 HU HU9802758A patent/HU225895B1/hu not_active IP Right Cessation
- 1998-11-27 CN CNB2004100435550A patent/CN1277807C/zh not_active Expired - Fee Related
- 1998-11-27 PL PL329989A patent/PL200436B1/pl unknown
- 1998-11-27 CN CNA2004100435584A patent/CN1550500A/zh active Pending
- 1998-11-27 CN CNB981230229A patent/CN1259306C/zh not_active Expired - Fee Related
-
2001
- 2001-01-30 US US09/772,501 patent/US6448402B2/en not_active Expired - Fee Related
-
2003
- 2003-10-29 US US10/695,930 patent/US7229981B2/en not_active Expired - Fee Related
-
2004
- 2004-03-08 IL IL16078704A patent/IL160787A0/xx active IP Right Grant
- 2004-10-14 NO NO20044369A patent/NO327575B1/no not_active IP Right Cessation
- 2004-10-14 NO NO20044368A patent/NO326251B1/no not_active IP Right Cessation
- 2004-10-14 NO NO20044370A patent/NO20044370L/no not_active Application Discontinuation
-
2005
- 2005-04-04 HK HK05102800A patent/HK1070103A1/xx not_active IP Right Cessation
- 2005-04-04 HK HK05102799A patent/HK1070050A1/xx not_active IP Right Cessation
-
2006
- 2006-01-26 KR KR1020060008435A patent/KR100648030B1/ko not_active IP Right Cessation
- 2006-01-26 KR KR1020060008436A patent/KR100672268B1/ko not_active IP Right Cessation
- 2006-01-26 KR KR1020060008437A patent/KR100584638B1/ko not_active IP Right Cessation
- 2006-05-31 US US11/421,266 patent/US7358073B2/en not_active Expired - Fee Related
- 2006-12-26 US US11/616,088 patent/US7338945B2/en not_active Expired - Fee Related
-
2009
- 2009-05-25 JP JP2009125243A patent/JP2009227684A/ja not_active Withdrawn
- 2009-05-25 JP JP2009125242A patent/JP2009221215A/ja not_active Ceased
- 2009-05-25 JP JP2009125244A patent/JP2009227685A/ja not_active Withdrawn
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO318697B1 (no) | Fremgangsmate for fremstilling av aminoalkoholderivater | |
US20050197503A1 (en) | Process for the preparation of N-alkyl-N-methyl-3-hydroxy-3-(2-thienyl)-propylamines | |
EP0397351B1 (en) | Preparation of diazabicyclic intermediates | |
KR960000758B1 (ko) | 광학적 활성 히드록시벤질아민 유도체 및 그의 제조방법 | |
EP0763005B1 (en) | TETRAHYDROINDENO[1,2-d][1,3,2]OXAZABOROLES AND THEIR USE AS ENANTIOSELECTIVE CATALYSTS | |
Zhong et al. | Asymmetric catalytic alkylation of vinyl azides with 3-bromo oxindoles: water-assisted chemo-and enantiocontrol | |
MX2010014510A (es) | Sintesis de aminas quirales. | |
IL147668A (en) | Process for the preparation of venlafaxin | |
EP0162444B1 (en) | Process for preparing rimantadine | |
CA1181085A (en) | Fluorinated amino-butyric acid and diaminobutane derivatives | |
FR2909376A1 (fr) | Procedes de preparation de la desmethulsertraline ou d'un de ses sels pharmaceutiquement acceptables | |
IE43132B1 (en) | Cis-bicyclooctyl-alkyl-amine derivatives | |
ES2349833T3 (es) | Procedimiento para la preparación de aminoalcoholes. | |
SK285271B6 (sk) | Spôsob výroby 4-[(2',5'-diamino-6'-halogénpyrimidin-4'- yl)amino]cyklopent-2-enylmetanolov | |
Nodzewska et al. | Synthesis of Solid-phase Supported Chiral Amines and Investigation of Stereoselectivity of Aldol Reactions of Amine-free Tropinone Enolate | |
JPH03157382A (ja) | 2―(2―チエニル)エチルアミンの製造法 | |
AU2022264993A1 (en) | Preparation method for pyrrole amide compound | |
CN114751853A (zh) | 6,6-二甲基-3-氮杂双环[3.1.0]己烷化合物的制备方法 | |
CN109665982A (zh) | 奈非西坦中间体2-吡咯烷酮的合成方法 | |
KR20030068853A (ko) | 신남산 유도체의 제조방법 | |
JPS63238066A (ja) | イミダゾリジン誘導体の製造法 | |
MXPA98009879A (es) | Procedimiento para la preparacion de derivados de aminoalcohol y su conversion adicional a (1r,4s)-4-((2-amino-6-cloro-5-formamido-4-pirimidinil)-amino)-2-ciclopenten-1-metanol | |
FR2935141A1 (fr) | Procede de preparation de l'ester ethylique de l'acide 4-[trans-4-[(phenylmethyl)-amino]cyclohexyl]benzoique et de son sel hemifumarate | |
JPH01149747A (ja) | テルペンジオール誘導体の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |