NO324679B1 - (1S,4R)- eller (1R,4S)-4-(2-amino-6-klor-9H-pyrin-9-yl)-2-cyklopenten-1-metanol og fremgangsmate for fremstilling av slike. - Google Patents
(1S,4R)- eller (1R,4S)-4-(2-amino-6-klor-9H-pyrin-9-yl)-2-cyklopenten-1-metanol og fremgangsmate for fremstilling av slike. Download PDFInfo
- Publication number
- NO324679B1 NO324679B1 NO19982149A NO982149A NO324679B1 NO 324679 B1 NO324679 B1 NO 324679B1 NO 19982149 A NO19982149 A NO 19982149A NO 982149 A NO982149 A NO 982149A NO 324679 B1 NO324679 B1 NO 324679B1
- Authority
- NO
- Norway
- Prior art keywords
- cyclopentene
- amino
- formula
- hydroxymethyl
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 31
- 230000008569 process Effects 0.000 title claims description 13
- -1 carboxylic acid halide Chemical class 0.000 claims abstract description 22
- 230000010933 acylation Effects 0.000 claims abstract description 11
- 238000005917 acylation reaction Methods 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 230000009467 reduction Effects 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
- XVSYDLITVYBCBD-UHFFFAOYSA-N cyclopent-3-ene-1-carboxylic acid Chemical class OC(=O)C1CC=CC1 XVSYDLITVYBCBD-UHFFFAOYSA-N 0.000 claims abstract description 6
- LMYOLOWXQDLHKQ-UHFFFAOYSA-N cyclopent-2-en-1-ylmethanol Chemical class OCC1CCC=C1 LMYOLOWXQDLHKQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 30
- 244000005700 microbiome Species 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
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- 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 claims description 11
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- 241000588986 Alcaligenes Species 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 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 claims description 6
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- UXKZFJDNFBNQHE-NTSWFWBYSA-N [(1r,4s)-4-aminocyclopent-2-en-1-yl]methanol Chemical compound N[C@H]1C[C@@H](CO)C=C1 UXKZFJDNFBNQHE-NTSWFWBYSA-N 0.000 claims description 5
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- 241000194107 Bacillus megaterium Species 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
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- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 3
- 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 claims description 3
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- 239000012467 final product Substances 0.000 claims description 2
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- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 claims 4
- 239000002253 acid Substances 0.000 abstract description 17
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- VTCHZFWYUPZZKL-UHFFFAOYSA-N 4-azaniumylcyclopent-2-ene-1-carboxylate Chemical compound NC1CC(C(O)=O)C=C1 VTCHZFWYUPZZKL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- UXKZFJDNFBNQHE-UHFFFAOYSA-N (4-aminocyclopent-2-en-1-yl)methanol Chemical class NC1CC(CO)C=C1 UXKZFJDNFBNQHE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
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- 239000000243 solution Substances 0.000 description 24
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 16
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- 241000187561 Rhodococcus erythropolis Species 0.000 description 12
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- 239000000284 extract Substances 0.000 description 11
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- 239000007983 Tris buffer Substances 0.000 description 9
- 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 9
- 239000011780 sodium chloride Substances 0.000 description 9
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- 150000007513 acids Chemical class 0.000 description 8
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- 239000000758 substrate Substances 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 7
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- 238000012163 sequencing technique Methods 0.000 description 6
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07C231/16—Preparation of optical isomers
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
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- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH111697 | 1997-05-13 | ||
| CH274097 | 1997-11-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO982149D0 NO982149D0 (no) | 1998-05-12 |
| NO982149L NO982149L (no) | 1998-11-16 |
| NO324679B1 true NO324679B1 (no) | 2007-12-03 |
Family
ID=25686703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19982149A NO324679B1 (no) | 1997-05-13 | 1998-05-12 | (1S,4R)- eller (1R,4S)-4-(2-amino-6-klor-9H-pyrin-9-yl)-2-cyklopenten-1-metanol og fremgangsmate for fremstilling av slike. |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US6156893A (sk) |
| EP (2) | EP0878548B1 (sk) |
| JP (3) | JP4540136B2 (sk) |
| KR (2) | KR100577886B1 (sk) |
| CN (2) | CN1115343C (sk) |
| AT (1) | ATE275206T1 (sk) |
| CA (1) | CA2237297C (sk) |
| CZ (3) | CZ297894B6 (sk) |
| DE (1) | DE59811884D1 (sk) |
| DK (1) | DK0878548T3 (sk) |
| ES (1) | ES2223095T3 (sk) |
| HK (1) | HK1092782A1 (sk) |
| HU (1) | HU226327B1 (sk) |
| NO (1) | NO324679B1 (sk) |
| PL (1) | PL197848B1 (sk) |
| PT (1) | PT878548E (sk) |
| SK (3) | SK284810B6 (sk) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1041631C (zh) * | 1993-06-21 | 1999-01-13 | 默里尔药物公司 | 用作炎症前细胞因子选择性抑制剂的新的碳环核苷药物 |
| 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 |
| CZ298144B6 (cs) * | 1997-11-27 | 2007-07-04 | Lonza Ag | Zpusob výroby (1S,4R)- nebo (1R,4S)-4-(2-amino-6-chlor-9-H-purin-9-yl)-2-cyklopenten-1-methanolu |
| HUP0104547A3 (en) * | 1998-12-23 | 2003-12-29 | Lonza Ag | Method for producing optically active 1-amino-4-(hydroxymethyl)-cyclopent-2-ene derivatives |
| MXPA06000945A (es) * | 2003-07-25 | 2006-03-30 | Prometic Biosciences Inc | Preparacion de sales metalicas de acidos grasos de cadena mediana. |
| 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 |
| US8795979B2 (en) | 2011-01-18 | 2014-08-05 | General Atomics | Hydrolase enzyme substrates and uses thereof |
| 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 |
|---|---|---|---|---|
| US4931559A (en) * | 1988-01-20 | 1990-06-05 | Regents Of The University Of Minnesota | Optically-active isomers of dideoxycarbocyclic nucleosides |
| US4950758A (en) * | 1988-01-20 | 1990-08-21 | 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 |
| CN1224697C (zh) * | 1996-05-30 | 2005-10-26 | 隆萨股份公司 | 氨基醇及其衍生物的制备方法 |
| GB9625455D0 (en) * | 1996-12-07 | 1997-01-22 | Glaxo Group Ltd | Process for resolving mixtures of carbocyclic steroisomers |
-
1998
- 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
- 1998-05-04 SK SK53-2005A patent/SK285228B6/sk not_active IP Right Cessation
- 1998-05-06 US US09/073,553 patent/US6156893A/en not_active Expired - Fee Related
- 1998-05-11 KR KR1019980016803A patent/KR100577886B1/ko not_active IP Right Cessation
- 1998-05-11 CZ CZ0145898A patent/CZ297894B6/cs not_active IP Right Cessation
- 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
- 1998-05-12 JP JP12933898A patent/JP4540136B2/ja not_active Expired - Fee Related
- 1998-05-12 NO NO19982149A patent/NO324679B1/no 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 CN CNB03123433XA patent/CN1302116C/zh not_active Expired - Fee Related
- 1998-05-13 AT AT98108721T patent/ATE275206T1/de active
- 1998-05-13 EP EP98108721A patent/EP0878548B1/de not_active Expired - Lifetime
- 1998-05-13 DK DK98108721T patent/DK0878548T3/da active
- 1998-05-13 ES ES98108721T patent/ES2223095T3/es not_active Expired - Lifetime
- 1998-05-13 HU HU9801083A patent/HU226327B1/hu not_active IP Right Cessation
- 1998-05-13 PL PL326267A patent/PL197848B1/pl not_active IP Right Cessation
- 1998-05-13 DE DE59811884T patent/DE59811884D1/de not_active Expired - Lifetime
- 1998-05-13 EP EP04020273A patent/EP1502914A1/de not_active Withdrawn
-
1999
- 1999-08-13 US US09/373,857 patent/US6252112B1/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 US09/373,856 patent/US6262295B1/en not_active Expired - Fee Related
-
2005
- 2005-10-19 KR KR1020050098642A patent/KR100601764B1/ko not_active IP Right Cessation
-
2006
- 2006-12-07 HK HK06113474.2A patent/HK1092782A1/xx not_active IP Right Cessation
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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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