ZA200505760B - Method for producing the enantiomeric forms of cis1,3,-cyclohexanediol derivatives - Google Patents
Method for producing the enantiomeric forms of cis1,3,-cyclohexanediol derivatives Download PDFInfo
- Publication number
- ZA200505760B ZA200505760B ZA200505760A ZA200505760A ZA200505760B ZA 200505760 B ZA200505760 B ZA 200505760B ZA 200505760 A ZA200505760 A ZA 200505760A ZA 200505760 A ZA200505760 A ZA 200505760A ZA 200505760 B ZA200505760 B ZA 200505760B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- formula
- alk
- compound
- defined above
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000006239 protecting group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 238000006460 hydrolysis reaction Methods 0.000 claims description 18
- 230000007073 chemical hydrolysis Effects 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- -1 O-(C1-Cg)-alkyl Chemical group 0.000 claims description 15
- 230000007071 enzymatic hydrolysis Effects 0.000 claims description 14
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 230000029936 alkylation Effects 0.000 claims description 11
- 238000005804 alkylation reaction Methods 0.000 claims description 11
- 230000002255 enzymatic effect Effects 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000010931 ester hydrolysis Methods 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 150000003536 tetrazoles Chemical class 0.000 claims description 8
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 230000000707 stereoselective effect Effects 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- RLMGYIOTPQVQJR-OLQVQODUSA-N (1s,3r)-cyclohexane-1,3-diol Chemical compound O[C@H]1CCC[C@@H](O)C1 RLMGYIOTPQVQJR-OLQVQODUSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000011445 neoadjuvant hormone therapy Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 101100133572 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nog-2 gene Proteins 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical class OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- QREBDIAGMMUKFO-UHFFFAOYSA-N s-ethyl octanethioate Chemical compound CCCCCCCC(=O)SCC QREBDIAGMMUKFO-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10308350A DE10308350B4 (de) | 2003-02-27 | 2003-02-27 | Verfahren zur Herstellung der enantiomeren Formen von cis-konfigurierten 1,3-Cyclohexandiol-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505760B true ZA200505760B (en) | 2006-05-31 |
Family
ID=32863920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505760A ZA200505760B (en) | 2003-02-27 | 2005-07-19 | Method for producing the enantiomeric forms of cis1,3,-cyclohexanediol derivatives |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1599433B1 (es) |
| JP (1) | JP2006519001A (es) |
| KR (1) | KR20050107469A (es) |
| CN (1) | CN100572348C (es) |
| AR (1) | AR044501A1 (es) |
| AT (1) | ATE347543T1 (es) |
| AU (1) | AU2004215674B2 (es) |
| BR (1) | BRPI0407844A (es) |
| CA (1) | CA2516623A1 (es) |
| CO (1) | CO5690547A2 (es) |
| CY (1) | CY1106454T1 (es) |
| DE (2) | DE10308350B4 (es) |
| DK (1) | DK1599433T3 (es) |
| ES (1) | ES2278305T3 (es) |
| HK (1) | HK1088889A1 (es) |
| IL (1) | IL170310A (es) |
| MX (1) | MXPA05009053A (es) |
| NO (1) | NO20054456L (es) |
| NZ (1) | NZ542025A (es) |
| PL (1) | PL377812A1 (es) |
| PT (1) | PT1599433E (es) |
| RU (1) | RU2372319C2 (es) |
| TW (1) | TWI331138B (es) |
| WO (1) | WO2004076390A1 (es) |
| ZA (1) | ZA200505760B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004038403B4 (de) * | 2004-08-07 | 2006-08-31 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung der enantiomeren Formen von cis-konfigurierten 3-Hydroxycyclohexancarbonsäure-Derivaten |
| DE102004040736B4 (de) * | 2004-08-23 | 2007-01-11 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Diarylcycloalkylderivaten |
| CN101381302B (zh) * | 2007-09-07 | 2013-04-03 | 上海睿智化学研究有限公司 | 2-溴甲基-6-甲基苯甲酰氯/溴的制备方法 |
| EP2679570A3 (en) | 2008-05-21 | 2014-07-02 | Taisho Pharmaceutical Co., Ltd. | Method of producing bicyclo[3.1.0]hexane derivative |
| BR112019016775A2 (pt) | 2017-02-17 | 2020-03-31 | Trevena, Inc. | Compostos moduladores de receptor delta-opioide contendo aza-heterocíclico com 7 membros, métodos de uso e produção dos mesmos |
| WO2023070605A1 (en) * | 2021-10-29 | 2023-05-04 | Trevena, Inc. | Methods of preparing 6-membered aza-heterocyclic containing delta-opioid receptor modulating compounds |
| CN114891838B (zh) * | 2022-04-29 | 2023-09-08 | 株洲壹诺生物技术有限公司 | 盐酸多佐胺中间体(s)-3-(2-噻吩硫基)-丁酸的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000064876A1 (en) * | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
| DE10004926A1 (de) * | 2000-02-04 | 2001-08-09 | Gruenenthal Gmbh | Verfahren zur enzymatischen Racematspaltung von Aminomethyl-Aryl-Cyclohexanol-Derivaten |
| CA2458210C (en) * | 2001-08-31 | 2011-09-20 | Aventis Pharma Deutschland Gmbh | Diaryl cycloalkyl derivatives, method for producing the same and the use thereof as ppar-activators |
-
2003
- 2003-02-27 DE DE10308350A patent/DE10308350B4/de not_active Expired - Fee Related
-
2004
- 2004-02-19 AU AU2004215674A patent/AU2004215674B2/en not_active Ceased
- 2004-02-19 BR BRPI0407844-6A patent/BRPI0407844A/pt not_active IP Right Cessation
- 2004-02-19 PT PT04712518T patent/PT1599433E/pt unknown
- 2004-02-19 DE DE502004002234T patent/DE502004002234D1/de not_active Expired - Lifetime
- 2004-02-19 KR KR1020057016034A patent/KR20050107469A/ko not_active Application Discontinuation
- 2004-02-19 CN CNB2004800054415A patent/CN100572348C/zh not_active Expired - Fee Related
- 2004-02-19 JP JP2006501887A patent/JP2006519001A/ja active Pending
- 2004-02-19 EP EP04712518A patent/EP1599433B1/de not_active Expired - Lifetime
- 2004-02-19 NZ NZ542025A patent/NZ542025A/en unknown
- 2004-02-19 MX MXPA05009053A patent/MXPA05009053A/es active IP Right Grant
- 2004-02-19 AT AT04712518T patent/ATE347543T1/de not_active IP Right Cessation
- 2004-02-19 RU RU2005129993/04A patent/RU2372319C2/ru not_active IP Right Cessation
- 2004-02-19 ES ES04712518T patent/ES2278305T3/es not_active Expired - Lifetime
- 2004-02-19 PL PL377812A patent/PL377812A1/pl not_active IP Right Cessation
- 2004-02-19 WO PCT/EP2004/001580 patent/WO2004076390A1/de active IP Right Grant
- 2004-02-19 CA CA002516623A patent/CA2516623A1/en not_active Abandoned
- 2004-02-19 DK DK04712518T patent/DK1599433T3/da active
- 2004-02-25 TW TW093104706A patent/TWI331138B/zh not_active IP Right Cessation
- 2004-02-27 AR ARP040100630A patent/AR044501A1/es unknown
-
2005
- 2005-07-19 ZA ZA200505760A patent/ZA200505760B/en unknown
- 2005-08-16 IL IL170310A patent/IL170310A/en not_active IP Right Cessation
- 2005-08-26 CO CO05085518A patent/CO5690547A2/es not_active Application Discontinuation
- 2005-09-26 NO NO20054456A patent/NO20054456L/no not_active Application Discontinuation
-
2006
- 2006-08-21 HK HK06109224.3A patent/HK1088889A1/xx not_active IP Right Cessation
-
2007
- 2007-03-05 CY CY20071100303T patent/CY1106454T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0407844A (pt) | 2006-02-14 |
| DE10308350B4 (de) | 2006-06-01 |
| EP1599433A1 (de) | 2005-11-30 |
| RU2372319C2 (ru) | 2009-11-10 |
| DK1599433T3 (da) | 2007-04-16 |
| DE10308350A1 (de) | 2004-09-16 |
| ATE347543T1 (de) | 2006-12-15 |
| CN1753855A (zh) | 2006-03-29 |
| DE502004002234D1 (de) | 2007-01-18 |
| NZ542025A (en) | 2009-03-31 |
| TW200508392A (en) | 2005-03-01 |
| IL170310A (en) | 2010-06-16 |
| ES2278305T3 (es) | 2007-08-01 |
| RU2005129993A (ru) | 2006-01-27 |
| CN100572348C (zh) | 2009-12-23 |
| NO20054456L (no) | 2005-09-26 |
| TWI331138B (en) | 2010-10-01 |
| EP1599433B1 (de) | 2006-12-06 |
| PL377812A1 (pl) | 2006-02-20 |
| HK1088889A1 (en) | 2006-11-17 |
| CO5690547A2 (es) | 2006-10-31 |
| CY1106454T1 (el) | 2011-10-12 |
| AU2004215674A1 (en) | 2004-09-10 |
| AR044501A1 (es) | 2005-09-14 |
| AU2004215674B2 (en) | 2010-02-04 |
| JP2006519001A (ja) | 2006-08-24 |
| MXPA05009053A (es) | 2005-10-19 |
| KR20050107469A (ko) | 2005-11-11 |
| CA2516623A1 (en) | 2004-09-10 |
| PT1599433E (pt) | 2007-02-28 |
| WO2004076390A1 (de) | 2004-09-10 |
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