SK278678B6 - Method of separating enantiomers of 5-hetaryl-1,3,4- -thiadiazinones - Google Patents
Method of separating enantiomers of 5-hetaryl-1,3,4- -thiadiazinones Download PDFInfo
- Publication number
- SK278678B6 SK278678B6 SK2634-92A SK263492A SK278678B6 SK 278678 B6 SK278678 B6 SK 278678B6 SK 263492 A SK263492 A SK 263492A SK 278678 B6 SK278678 B6 SK 278678B6
- Authority
- SK
- Slovakia
- Prior art keywords
- general formula
- mixture
- splitting
- diastereomer
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 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 title claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 239000012442 inert solvent Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- SNKAAIQBOBROQQ-UHFFFAOYSA-N 4,7-dimethylbicyclo[2.2.1]heptane-7-carbonyl chloride Chemical compound C1CC2CCC1(C)C2(C)C(Cl)=O SNKAAIQBOBROQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 12
- 239000002253 acid Substances 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 glycol dialkylethers Chemical class 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MONYKFFREQWXHY-UHFFFAOYSA-N 6-methyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CC1SC(=O)NN=C1 MONYKFFREQWXHY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JDFOIACPOPEQLS-UHFFFAOYSA-N 1,2,2,3-tetramethylcyclopentane-1-carboxylic acid Chemical compound CC1CCC(C)(C(O)=O)C1(C)C JDFOIACPOPEQLS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KZKKRAVNYHSDCG-UHFFFAOYSA-N 2-(2-acetylphenyl)-2-hydroxyacetyl chloride Chemical compound CC(=O)C1=CC=CC=C1C(O)C(Cl)=O KZKKRAVNYHSDCG-UHFFFAOYSA-N 0.000 description 1
- FCVBPUAYGGSBCT-UHFFFAOYSA-N 5-[1-(1,3-benzodioxole-5-carbonyl)-3,4-dihydro-2h-quinolin-6-yl]-6-methyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CC1SC(=O)NN=C1C1=CC=C(N(CCC2)C(=O)C=3C=C4OCOC4=CC=3)C2=C1 FCVBPUAYGGSBCT-UHFFFAOYSA-N 0.000 description 1
- NNDIFJWAEOADAZ-UHFFFAOYSA-N 5-oxooxolane-2-carbonyl chloride Chemical compound ClC(=O)C1CCC(=O)O1 NNDIFJWAEOADAZ-UHFFFAOYSA-N 0.000 description 1
- NDSAOXAHKUFRIT-UHFFFAOYSA-N 6-methyl-5-[1-(3,4,5-trimethoxybenzoyl)-3,4-dihydro-2h-quinolin-6-yl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2C3=CC=C(C=C3CCC2)C=2C(SC(=O)NN=2)C)=C1 NDSAOXAHKUFRIT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4129062A DE4129062A1 (de) | 1991-09-02 | 1991-09-02 | Verfahren zur enantiomerentrennung von 5-hetaryl-1,3,4-thiadiazinonen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK263492A3 SK263492A3 (en) | 1997-12-10 |
| SK278678B6 true SK278678B6 (en) | 1997-12-10 |
Family
ID=6439631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK2634-92A SK278678B6 (en) | 1991-09-02 | 1992-08-26 | Method of separating enantiomers of 5-hetaryl-1,3,4- -thiadiazinones |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5206363A (cs) |
| EP (1) | EP0530657B1 (cs) |
| JP (1) | JPH05202041A (cs) |
| KR (1) | KR930006016A (cs) |
| AT (1) | ATE144982T1 (cs) |
| AU (1) | AU658215B2 (cs) |
| CA (1) | CA2077031A1 (cs) |
| CZ (1) | CZ281376B6 (cs) |
| DE (2) | DE4129062A1 (cs) |
| DK (1) | DK0530657T3 (cs) |
| ES (1) | ES2095992T3 (cs) |
| GR (1) | GR3022443T3 (cs) |
| HU (1) | HU212178B (cs) |
| MX (1) | MX9204972A (cs) |
| NO (1) | NO300498B1 (cs) |
| PL (1) | PL169606B1 (cs) |
| RU (1) | RU2053231C1 (cs) |
| SK (1) | SK278678B6 (cs) |
| TW (1) | TW234113B (cs) |
| ZA (1) | ZA926617B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500558A1 (de) * | 1995-01-11 | 1996-07-18 | Merck Patent Gmbh | 3-Alkoxycarbonyl-thiadiazinone |
| DE19707641C1 (de) * | 1997-02-26 | 1998-03-26 | Merck Patent Gmbh | Enantiomerentrennung von 5-Hetaryl-1,3,4-thiadiazinonen |
| DE19929785A1 (de) * | 1999-06-29 | 2001-01-04 | Bayer Ag | Tetrahydrochinolinyl-6-methyldihydrothiadiazinon-Derivate und ihre Verwendung |
| WO2001051089A1 (de) * | 2000-01-13 | 2001-07-19 | Merck Patent Gmbh | Pharmazeutische zubereitungen enthaltend 2-pyrrolidon als lösungsvermittler |
| US7741317B2 (en) * | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL77031A (en) * | 1985-11-12 | 1995-12-08 | Yeda Res & Dev | Kinetic resolution of racemic mixtures by polymer-bound crystallization inhibitors |
| US4716246A (en) * | 1986-08-22 | 1987-12-29 | Merck & Co., Inc. | Process for L-dopa |
| AU614965B2 (en) * | 1987-06-06 | 1991-09-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Thiadiazinones |
-
1991
- 1991-09-02 DE DE4129062A patent/DE4129062A1/de not_active Withdrawn
-
1992
- 1992-08-26 CZ CS922634A patent/CZ281376B6/cs unknown
- 1992-08-26 EP EP92114505A patent/EP0530657B1/de not_active Expired - Lifetime
- 1992-08-26 ES ES92114505T patent/ES2095992T3/es not_active Expired - Lifetime
- 1992-08-26 DK DK92114505.8T patent/DK0530657T3/da active
- 1992-08-26 DE DE59207484T patent/DE59207484D1/de not_active Expired - Fee Related
- 1992-08-26 AT AT92114505T patent/ATE144982T1/de not_active IP Right Cessation
- 1992-08-26 SK SK2634-92A patent/SK278678B6/sk unknown
- 1992-08-28 JP JP4230117A patent/JPH05202041A/ja active Pending
- 1992-08-28 MX MX9204972A patent/MX9204972A/es not_active IP Right Cessation
- 1992-08-31 TW TW081106888A patent/TW234113B/zh active
- 1992-08-31 CA CA002077031A patent/CA2077031A1/en not_active Abandoned
- 1992-09-01 AU AU22051/92A patent/AU658215B2/en not_active Ceased
- 1992-09-01 RU SU925052318A patent/RU2053231C1/ru active
- 1992-09-01 KR KR1019920015824A patent/KR930006016A/ko not_active Ceased
- 1992-09-01 HU HU9202806A patent/HU212178B/hu not_active IP Right Cessation
- 1992-09-01 ZA ZA926617A patent/ZA926617B/xx unknown
- 1992-09-01 PL PL92295804A patent/PL169606B1/pl unknown
- 1992-09-01 NO NO923412A patent/NO300498B1/no unknown
- 1992-09-02 US US07/939,754 patent/US5206363A/en not_active Expired - Fee Related
-
1997
- 1997-01-30 GR GR970400158T patent/GR3022443T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5206363A (en) | 1993-04-27 |
| CA2077031A1 (en) | 1993-03-03 |
| HU9202806D0 (en) | 1992-11-30 |
| DE4129062A1 (de) | 1993-03-04 |
| DE59207484D1 (de) | 1996-12-12 |
| MX9204972A (es) | 1993-03-01 |
| ZA926617B (en) | 1993-03-25 |
| KR930006016A (ko) | 1993-04-20 |
| HUT63414A (en) | 1993-08-30 |
| HU212178B (en) | 1996-03-28 |
| CZ281376B6 (cs) | 1996-09-11 |
| RU2053231C1 (ru) | 1996-01-27 |
| AU2205192A (en) | 1993-03-11 |
| SK263492A3 (en) | 1997-12-10 |
| TW234113B (cs) | 1994-11-11 |
| AU658215B2 (en) | 1995-04-06 |
| GR3022443T3 (en) | 1997-04-30 |
| JPH05202041A (ja) | 1993-08-10 |
| ES2095992T3 (es) | 1997-03-01 |
| EP0530657A1 (de) | 1993-03-10 |
| NO300498B1 (no) | 1997-06-09 |
| NO923412D0 (no) | 1992-09-01 |
| ATE144982T1 (de) | 1996-11-15 |
| CZ263492A3 (en) | 1993-03-17 |
| EP0530657B1 (de) | 1996-11-06 |
| PL295804A2 (en) | 1993-03-08 |
| NO923412L (no) | 1993-03-03 |
| DK0530657T3 (da) | 1997-04-07 |
| PL169606B1 (pl) | 1996-08-30 |
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