SK282782B6 - Spôsob výroby v podstate enantiomérne čistého N-chráneného (1R,4S)-2-azabicyklo[2.2.1]hept-5-en-3-ónu - Google Patents
Spôsob výroby v podstate enantiomérne čistého N-chráneného (1R,4S)-2-azabicyklo[2.2.1]hept-5-en-3-ónu Download PDFInfo
- Publication number
- SK282782B6 SK282782B6 SK1844-99A SK184499A SK282782B6 SK 282782 B6 SK282782 B6 SK 282782B6 SK 184499 A SK184499 A SK 184499A SK 282782 B6 SK282782 B6 SK 282782B6
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- process according
- hept
- group
- azabicyclo
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 150000003951 lactams Chemical class 0.000 title description 12
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 125000006239 protecting group Chemical group 0.000 claims abstract description 13
- 108700023418 Amidases Proteins 0.000 claims abstract description 10
- 230000003213 activating effect Effects 0.000 claims abstract description 10
- 102000005922 amidase Human genes 0.000 claims abstract description 10
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- -1 N-protected (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one Chemical class 0.000 claims abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 108010020132 microbial serine proteinases Proteins 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- DDUFYKNOXPZZIW-UHNVWZDZSA-N (1s,4r)-3-azabicyclo[2.2.1]hept-5-en-2-one Chemical compound C1[C@@H]2C(=O)N[C@H]1C=C2 DDUFYKNOXPZZIW-UHNVWZDZSA-N 0.000 claims description 4
- DDUFYKNOXPZZIW-CRCLSJGQSA-N vince lactam Chemical compound C1[C@H]2C(=O)N[C@@H]1C=C2 DDUFYKNOXPZZIW-CRCLSJGQSA-N 0.000 claims description 4
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 description 20
- 108090000790 Enzymes Proteins 0.000 description 20
- 229940088598 enzyme Drugs 0.000 description 16
- 238000004296 chiral HPLC Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 7
- 229960004748 abacavir Drugs 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000011942 biocatalyst Substances 0.000 description 4
- IHLRGGLJGGTPCY-HWKANZROSA-N (e)-hept-5-en-3-one Chemical compound CCC(=O)C\C=C\C IHLRGGLJGGTPCY-HWKANZROSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 241000228257 Aspergillus sp. Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108091005804 Peptidases Proteins 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NQIZWJGHIYDHRL-UHFFFAOYSA-N tert-butyl 2-oxo-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate Chemical compound C1C2C=CC1N(C(=O)OC(C)(C)C)C2=O NQIZWJGHIYDHRL-UHFFFAOYSA-N 0.000 description 3
- ZUMZWQHPSXZHBQ-NKWVEPMBSA-N (1r,4s)-3-acetyl-3-azabicyclo[2.2.1]hept-5-en-2-one Chemical compound C1[C@]2([H])C=C[C@@]1([H])N(C(C)=O)C2=O ZUMZWQHPSXZHBQ-NKWVEPMBSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010056079 Subtilisins Proteins 0.000 description 2
- 102000005158 Subtilisins Human genes 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000007073 chemical hydrolysis Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- JONIMGVUGJVFQD-UHFFFAOYSA-N (4-methylphenyl)sulfonylformonitrile Chemical compound CC1=CC=C(S(=O)(=O)C#N)C=C1 JONIMGVUGJVFQD-UHFFFAOYSA-N 0.000 description 1
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 description 1
- MCVRAVYDLNZUCY-UHFFFAOYSA-N 2-methylhept-5-enoic acid Chemical compound CC=CCCC(C)C(O)=O MCVRAVYDLNZUCY-UHFFFAOYSA-N 0.000 description 1
- DDUFYKNOXPZZIW-UHFFFAOYSA-N 3-azabicyclo[2.2.1]hept-5-en-2-one Chemical compound C1C2C(=O)NC1C=C2 DDUFYKNOXPZZIW-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000005593 Endopeptidases Human genes 0.000 description 1
- 108010059378 Endopeptidases Proteins 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 102000009127 Glutaminase Human genes 0.000 description 1
- 108010073324 Glutaminase Proteins 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 101001091385 Homo sapiens Kallikrein-6 Proteins 0.000 description 1
- 102100034866 Kallikrein-6 Human genes 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 101710118538 Protease Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000223258 Thermomyces lanuginosus Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- IHLRGGLJGGTPCY-UHFFFAOYSA-N hept-5-en-3-one Chemical class CCC(=O)CC=CC IHLRGGLJGGTPCY-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940040461 lipase Drugs 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 108010009355 microbial metalloproteinases Proteins 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940127073 nucleoside analogue Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
Classifications
-
- 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
-
- 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
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9717928.7A GB9717928D0 (en) | 1997-08-22 | 1997-08-22 | Process for the enatioselective hydrolysis of n-derivatised lactams |
| PCT/EP1998/005291 WO1999010519A1 (en) | 1997-08-22 | 1998-08-20 | Process for preparing enantiomerically enriched n-derivatised lactams |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK184499A3 SK184499A3 (en) | 2000-09-12 |
| SK282782B6 true SK282782B6 (sk) | 2002-12-03 |
Family
ID=10817952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1844-99A SK282782B6 (sk) | 1997-08-22 | 1998-08-20 | Spôsob výroby v podstate enantiomérne čistého N-chráneného (1R,4S)-2-azabicyklo[2.2.1]hept-5-en-3-ónu |
Country Status (34)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE258605T1 (de) * | 1998-07-09 | 2004-02-15 | Lonza Ag | Verfahren zur herstellung von (1r,4s)-2- azabicyclo 2.2.1 hept-5-en-3-on-derivaten |
| DE19962543A1 (de) | 1999-12-23 | 2001-07-05 | Degussa | Chromatographische Enantiomerentrennung von bicyclischen Lactamen |
| US6780635B2 (en) * | 2001-12-27 | 2004-08-24 | Council Of Scientific And Industrial Research | Process for the preparation of optically active azabicyclo heptanone derivatives |
| EP1348765B1 (en) * | 2002-03-28 | 2006-05-24 | Council of Scientific and Industrial Research | Process for the preparation of optically active azabicyclo heptanone derivatives |
| HU227663B1 (en) * | 2007-07-09 | 2011-10-28 | Univ Szegedi | Resolution process |
| EP3351249A1 (en) | 2010-01-27 | 2018-07-25 | VIIV Healthcare Company | Antiviral therapy |
| CN103695495B (zh) * | 2014-01-14 | 2014-08-27 | 营口三征新科技化工有限公司 | 一种制备(1R,4s)-(-)-2-氮杂双环[2,2,1]庚-5-烯-3-酮的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2067693T3 (es) | 1989-10-16 | 1995-04-01 | Chiroscience Ltd | Azabicicloheptanona quiral y un procedimiento para su preparacion. |
| GB9108384D0 (en) | 1991-04-19 | 1991-06-05 | Enzymatix Ltd | Bicycloheptanes |
| SK285228B6 (sk) * | 1997-05-13 | 2006-09-07 | Lonza Ag | Spôsob výroby racemického alebo opticky aktívnehoderivátu 4-(hydroxymetyl)-2-cyklopenténu a racemicky N-butyryl-1-amino-4- (hydroxymetyl)-2-cyklopentén |
-
1997
- 1997-08-22 GB GBGB9717928.7A patent/GB9717928D0/en active Pending
-
1998
- 1998-08-20 EP EP98951307A patent/EP1003903B1/en not_active Expired - Lifetime
- 1998-08-20 ES ES98951307T patent/ES2193568T3/es not_active Expired - Lifetime
- 1998-08-20 ID IDW991671A patent/ID25830A/id unknown
- 1998-08-20 SK SK1844-99A patent/SK282782B6/sk not_active IP Right Cessation
- 1998-08-20 US US09/446,587 patent/US6340587B1/en not_active Expired - Lifetime
- 1998-08-20 TR TR1999/03210T patent/TR199903210T2/xx unknown
- 1998-08-20 EE EEP200000075A patent/EE03934B1/xx unknown
- 1998-08-20 DE DE69811677T patent/DE69811677T2/de not_active Expired - Lifetime
- 1998-08-20 RS YUP-693/99A patent/RS49542B/sr unknown
- 1998-08-20 CZ CZ19994716A patent/CZ294302B6/cs not_active IP Right Cessation
- 1998-08-20 PT PT98951307T patent/PT1003903E/pt unknown
- 1998-08-20 BR BRPI9810472-1A patent/BR9810472B1/pt not_active IP Right Cessation
- 1998-08-20 DK DK98951307T patent/DK1003903T3/da active
- 1998-08-20 AP APAP/P/1999/001721A patent/AP1104A/en active
- 1998-08-20 EA EA199901059A patent/EA001964B1/ru not_active IP Right Cessation
- 1998-08-20 AT AT98951307T patent/ATE233323T1/de active
- 1998-08-20 SI SI9830407T patent/SI1003903T1/xx unknown
- 1998-08-20 CN CNB988064790A patent/CN1133749C/zh not_active Expired - Lifetime
- 1998-08-20 KR KR10-1999-7012114A patent/KR100479894B1/ko not_active Expired - Lifetime
- 1998-08-20 WO PCT/EP1998/005291 patent/WO1999010519A1/en not_active Ceased
- 1998-08-20 HR HR990408A patent/HRP990408B1/xx not_active IP Right Cessation
- 1998-08-20 AU AU97386/98A patent/AU738897B2/en not_active Expired
- 1998-08-20 NZ NZ501880A patent/NZ501880A/en not_active IP Right Cessation
- 1998-08-20 TW TW087113730A patent/TW589301B/zh not_active IP Right Cessation
- 1998-08-20 IL IL13354198A patent/IL133541A/xx not_active IP Right Cessation
- 1998-08-20 HU HU0002661A patent/HU222657B1/hu active IP Right Grant
- 1998-08-20 JP JP51391699A patent/JP3565868B2/ja not_active Expired - Lifetime
- 1998-08-20 CA CA002295017A patent/CA2295017A1/en not_active Abandoned
- 1998-08-20 PL PL337647A patent/PL191108B1/pl unknown
- 1998-08-21 IN IN1499CA1998 patent/IN183908B/en unknown
- 1998-08-21 AR ARP980104167A patent/AR016395A1/es active IP Right Grant
-
1999
- 1999-12-14 IS IS5297A patent/IS2201B/is unknown
- 1999-12-21 NO NO19996368A patent/NO320081B1/no not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20180820 |