SK285228B6 - Spôsob výroby racemického alebo opticky aktívnehoderivátu 4-(hydroxymetyl)-2-cyklopenténu a racemicky N-butyryl-1-amino-4- (hydroxymetyl)-2-cyklopentén - Google Patents
Spôsob výroby racemického alebo opticky aktívnehoderivátu 4-(hydroxymetyl)-2-cyklopenténu a racemicky N-butyryl-1-amino-4- (hydroxymetyl)-2-cyklopentén Download PDFInfo
- Publication number
- SK285228B6 SK285228B6 SK53-2005A SK532005A SK285228B6 SK 285228 B6 SK285228 B6 SK 285228B6 SK 532005 A SK532005 A SK 532005A SK 285228 B6 SK285228 B6 SK 285228B6
- Authority
- SK
- Slovakia
- Prior art keywords
- cyclopentene
- hydroxymethyl
- racemic
- amino
- optically active
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 9
- LMYOLOWXQDLHKQ-UHFFFAOYSA-N cyclopent-2-en-1-ylmethanol Chemical class OCC1CCC=C1 LMYOLOWXQDLHKQ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- PVRSHAUROLANIJ-UHFFFAOYSA-N n-[4-(hydroxymethyl)cyclopent-2-en-1-yl]butanamide Chemical compound CCCC(=O)NC1CC(CO)C=C1 PVRSHAUROLANIJ-UHFFFAOYSA-N 0.000 title description 6
- -1 carbonyl halide Chemical class 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
- XVSYDLITVYBCBD-UHFFFAOYSA-N cyclopent-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC=CC1 XVSYDLITVYBCBD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- PVRSHAUROLANIJ-BDAKNGLRSA-N n-[(1r,4s)-4-(hydroxymethyl)cyclopent-2-en-1-yl]butanamide Chemical compound CCCC(=O)N[C@@H]1C[C@H](CO)C=C1 PVRSHAUROLANIJ-BDAKNGLRSA-N 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- RMZJPEGRFQHGBT-UHFFFAOYSA-N tert-butyl carbonofluoridate Chemical compound CC(C)(C)OC(F)=O RMZJPEGRFQHGBT-UHFFFAOYSA-N 0.000 description 3
- WOUNTSATDZJBLP-SFYZADRCSA-N (1s,4r)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-ene-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)N[C@@H]1C[C@H](C(O)=O)C=C1 WOUNTSATDZJBLP-SFYZADRCSA-N 0.000 description 2
- IHLRGGLJGGTPCY-HWKANZROSA-N (e)-hept-5-en-3-one Chemical compound CCC(=O)C\C=C\C IHLRGGLJGGTPCY-HWKANZROSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WOUNTSATDZJBLP-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-ene-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1CC(C(O)=O)C=C1 WOUNTSATDZJBLP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DFJSXBUVSKWALM-IBTYICNHSA-N [(1s,4r)-4-aminocyclopent-2-en-1-yl]methanol;hydrochloride Chemical compound Cl.N[C@@H]1C[C@H](CO)C=C1 DFJSXBUVSKWALM-IBTYICNHSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- DDUFYKNOXPZZIW-UHFFFAOYSA-N 3-azabicyclo[2.2.1]hept-5-en-2-one Chemical group C1C2C(=O)NC1C=C2 DDUFYKNOXPZZIW-UHFFFAOYSA-N 0.000 description 1
- JYDJHYGBXSCMJL-UHFFFAOYSA-N 4-aminocyclopent-2-ene-1-carboxylic acid;hydrochloride Chemical compound Cl.NC1CC(C(O)=O)C=C1 JYDJHYGBXSCMJL-UHFFFAOYSA-N 0.000 description 1
- 125000006847 BOC protecting group Chemical group 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DFJSXBUVSKWALM-RIHPBJNCSA-N [(1r,4s)-4-aminocyclopent-2-en-1-yl]methanol;hydrochloride Chemical compound Cl.N[C@H]1C[C@@H](CO)C=C1 DFJSXBUVSKWALM-RIHPBJNCSA-N 0.000 description 1
- IHEDZPMXLKYPSA-RQJHMYQMSA-N [(1s,4r)-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-RQJHMYQMSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JVSLVBYLHIRGJQ-SFYZADRCSA-N n-[(1r,4s)-4-(hydroxymethyl)cyclopent-2-en-1-yl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](CO)C=C1 JVSLVBYLHIRGJQ-SFYZADRCSA-N 0.000 description 1
- PVRSHAUROLANIJ-DTWKUNHWSA-N n-[(1s,4r)-4-(hydroxymethyl)cyclopent-2-en-1-yl]butanamide Chemical compound CCCC(=O)N[C@H]1C[C@@H](CO)C=C1 PVRSHAUROLANIJ-DTWKUNHWSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 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 1
- MVIWPMBRXBNBDX-BDAKNGLRSA-N tert-butyl n-[(1r,4s)-4-(hydroxymethyl)cyclopent-2-en-1-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1C[C@H](CO)C=C1 MVIWPMBRXBNBDX-BDAKNGLRSA-N 0.000 description 1
- MVIWPMBRXBNBDX-UHFFFAOYSA-N tert-butyl n-[4-(hydroxymethyl)cyclopent-2-en-1-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CC(CO)C=C1 MVIWPMBRXBNBDX-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH111697 | 1997-05-13 | ||
| CH274097 | 1997-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK285228B6 true SK285228B6 (sk) | 2006-09-07 |
Family
ID=25686703
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK53-2005A SK285228B6 (sk) | 1997-05-13 | 1998-05-04 | Spôsob výroby racemického alebo opticky aktívnehoderivátu 4-(hydroxymetyl)-2-cyklopenténu a racemicky N-butyryl-1-amino-4- (hydroxymetyl)-2-cyklopentén |
| SK589-98A SK284810B6 (sk) | 1997-05-13 | 1998-05-04 | Spôsob výroby (1S,4R)- alebo (1R,4S)-4-(2-amino-6-chlór-9-H- purín-9-yl)-2-cyklopentén-1-metanolu |
| SK54-2005A SK285229B6 (sk) | 1997-05-13 | 1998-05-04 | 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 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK589-98A SK284810B6 (sk) | 1997-05-13 | 1998-05-04 | Spôsob výroby (1S,4R)- alebo (1R,4S)-4-(2-amino-6-chlór-9-H- purín-9-yl)-2-cyklopentén-1-metanolu |
| SK54-2005A SK285229B6 (sk) | 1997-05-13 | 1998-05-04 | 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 |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US6156893A (cs) |
| EP (2) | EP0878548B1 (cs) |
| JP (3) | JP4540136B2 (cs) |
| KR (2) | KR100577886B1 (cs) |
| CN (2) | CN1115343C (cs) |
| AT (1) | ATE275206T1 (cs) |
| CA (1) | CA2237297C (cs) |
| CZ (3) | CZ297887B6 (cs) |
| DE (1) | DE59811884D1 (cs) |
| DK (1) | DK0878548T3 (cs) |
| ES (1) | ES2223095T3 (cs) |
| HU (1) | HU226327B1 (cs) |
| NO (1) | NO324679B1 (cs) |
| PL (1) | PL197848B1 (cs) |
| PT (1) | PT878548E (cs) |
| SK (3) | SK285228B6 (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2165779C (en) * | 1993-06-21 | 1998-06-16 | Carl K. Edwards, Iii | Novel carbocyclic nucleoside agents useful as selective inhibitors of proinflammatory cytokines |
| GB9717928D0 (en) * | 1997-08-22 | 1997-10-29 | Glaxo Group Ltd | Process for the enatioselective hydrolysis of n-derivatised lactams |
| GB9721780D0 (en) * | 1997-10-14 | 1997-12-10 | Glaxo Group Ltd | Process for the synthesis of chloropurine intermediates |
| CZ298913B6 (cs) * | 1997-11-27 | 2008-03-12 | Lonza Ag | Zpusob výroby aminoalkoholu a jeho derivátu |
| MXPA01006428A (es) * | 1998-12-23 | 2002-06-21 | Lonza Ag | Procedimiento para la preparacion de derivados opticamente activos de 1-amino-4-(hidroximetil)-ciclopent-2-eno. |
| PT1648851E (pt) * | 2003-07-25 | 2007-05-31 | Prometic Biosciences Inc | Praparação de sais metálicos de ácidos gordos de cadeia média |
| DE102005061756B4 (de) * | 2005-12-21 | 2008-01-03 | Sanofi-Aventis Deutschland Gmbh | Verbessertes Verfahren zur Herstellung von Ramipril |
| US8236853B1 (en) | 2007-12-03 | 2012-08-07 | University Of South Florida | Formation of cyclopentene nitro-ester and derivatives |
| CN103889997B (zh) | 2011-01-18 | 2017-08-25 | 通用原子公司 | 水解酶酶底物及其应用 |
| CN102557990B (zh) * | 2011-04-25 | 2014-06-25 | 开原亨泰制药股份有限公司 | (1s，4r)n-叔丁氧羰基-4-氨基-2-环戊烯-1-羧酸甲酯的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4950758A (en) * | 1988-01-20 | 1990-08-21 | Regents Of The University Of Minnesota | Optically-active isomers of dideoxycarbocyclic nucleosides |
| US4931559A (en) * | 1988-01-20 | 1990-06-05 | Regents Of The University Of Minnesota | Optically-active isomers of dideoxycarbocyclic nucleosides |
| MY104575A (en) * | 1989-12-22 | 1994-04-30 | The Wellcome Foundation Ltd | Therapeutic nucleosides. |
| CA2055086A1 (en) * | 1991-02-12 | 1992-08-13 | Chikara Kaneko | Cyclopentene derivatives and their use |
| 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 |
| GB9204015D0 (en) * | 1992-02-25 | 1992-04-08 | Wellcome Found | Therapeutic nucleosides |
| GB9205071D0 (en) * | 1992-03-09 | 1992-04-22 | Wellcome Found | Therapeutic nucleosides |
| GB9217823D0 (en) * | 1992-08-21 | 1992-10-07 | Glaxo Group Ltd | Chemical process |
| JPH06116217A (ja) * | 1992-10-02 | 1994-04-26 | Kuraray Co Ltd | （±）−シス−４−アミノシクロペント−２−エンカルボン酸誘導体の光学分割法 |
| GB9402161D0 (en) * | 1994-02-04 | 1994-03-30 | Wellcome Found | Chloropyrimidine intermediates |
| CA2253977C (en) * | 1996-05-30 | 2009-08-04 | Lonza Ag | Process for the preparation of amino alcohols and derivatives thereof |
| GB9625455D0 (en) * | 1996-12-07 | 1997-01-22 | Glaxo Group Ltd | Process for resolving mixtures of carbocyclic steroisomers |
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1998
- 1998-05-04 SK SK53-2005A patent/SK285228B6/sk not_active IP Right Cessation
- 1998-05-04 SK SK589-98A patent/SK284810B6/sk not_active IP Right Cessation
- 1998-05-04 SK SK54-2005A patent/SK285229B6/sk not_active IP Right Cessation
- 1998-05-06 US US09/073,553 patent/US6156893A/en not_active Expired - Fee Related
- 1998-05-11 CZ CZ20060694A patent/CZ297887B6/cs not_active IP Right Cessation
- 1998-05-11 CZ CZ20060695A patent/CZ297888B6/cs not_active IP Right Cessation
- 1998-05-11 CA CA002237297A patent/CA2237297C/en not_active Expired - Fee Related
- 1998-05-11 KR KR1019980016803A patent/KR100577886B1/ko not_active Expired - Fee Related
- 1998-05-11 CZ CZ0145898A patent/CZ297894B6/cs not_active IP Right Cessation
- 1998-05-12 NO NO19982149A patent/NO324679B1/no not_active IP Right Cessation
- 1998-05-12 JP JP12933898A patent/JP4540136B2/ja not_active Expired - Fee Related
- 1998-05-13 DE DE59811884T patent/DE59811884D1/de not_active Expired - Lifetime
- 1998-05-13 HU HU9801083A patent/HU226327B1/hu not_active IP Right Cessation
- 1998-05-13 CN CN98108865A patent/CN1115343C/zh not_active Expired - Fee Related
- 1998-05-13 PT PT98108721T patent/PT878548E/pt unknown
- 1998-05-13 EP EP98108721A patent/EP0878548B1/de not_active Expired - Lifetime
- 1998-05-13 PL PL326267A patent/PL197848B1/pl not_active IP Right Cessation
- 1998-05-13 DK DK98108721T patent/DK0878548T3/da active
- 1998-05-13 AT AT98108721T patent/ATE275206T1/de active
- 1998-05-13 CN CNB03123433XA patent/CN1302116C/zh not_active Expired - Fee Related
- 1998-05-13 EP EP04020273A patent/EP1502914A1/de not_active Withdrawn
- 1998-05-13 ES ES98108721T patent/ES2223095T3/es not_active Expired - Lifetime
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1999
- 1999-08-13 US US09/373,856 patent/US6262295B1/en not_active Expired - Fee Related
- 1999-08-13 US US09/373,862 patent/US6137007A/en not_active Expired - Fee Related
- 1999-08-13 US US09/373,857 patent/US6252112B1/en not_active Expired - Fee Related
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2005
- 2005-10-19 KR KR1020050098642A patent/KR100601764B1/ko not_active Expired - Fee Related
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2009
- 2009-11-09 JP JP2009256399A patent/JP2010106025A/ja active Pending
- 2009-11-09 JP JP2009256398A patent/JP2010116397A/ja active Pending
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| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20120504 |