HU211271A9 - New optical isomers - Google Patents
New optical isomers Download PDFInfo
- Publication number
- HU211271A9 HU211271A9 HU95P/P00421P HU9500421P HU211271A9 HU 211271 A9 HU211271 A9 HU 211271A9 HU 9500421 P HU9500421 P HU 9500421P HU 211271 A9 HU211271 A9 HU 211271A9
- Authority
- HU
- Hungary
- Prior art keywords
- imidazole
- dihydro
- fluoro
- inden
- enantiomer
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title description 6
- SRTZGTVJBSGUPX-UHFFFAOYSA-N 5-(5-fluoro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole Chemical compound C1C2=CC(F)=CC=C2CC1C1=CNC=N1 SRTZGTVJBSGUPX-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000001358 L(+)-tartaric acid Substances 0.000 claims description 3
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims description 3
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000011833 salt mixture Substances 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 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 9
- 241000700159 Rattus Species 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000008485 antagonism Effects 0.000 description 6
- 230000015654 memory Effects 0.000 description 6
- 239000000556 agonist Substances 0.000 description 5
- -1 formals Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- HSWPZIDYAHLZDD-UHFFFAOYSA-N atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 description 4
- 229960003002 atipamezole Drugs 0.000 description 4
- 208000010877 cognitive disease Diseases 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- POPGTFGTDBMAIP-UHFFFAOYSA-N 5-(5-nitro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole Chemical compound C1C2=CC([N+](=O)[O-])=CC=C2CC1C1=CNC=N1 POPGTFGTDBMAIP-UHFFFAOYSA-N 0.000 description 3
- 108060003345 Adrenergic Receptor Proteins 0.000 description 3
- 102000017910 Adrenergic receptor Human genes 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000008484 agonism Effects 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JXMXDKHEZLKQPB-UHFFFAOYSA-N detomidine Chemical compound CC1=CC=CC(CC=2[N]C=NC=2)=C1C JXMXDKHEZLKQPB-UHFFFAOYSA-N 0.000 description 2
- 229960001894 detomidine Drugs 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QHDUJTCUPWHNPK-UHFFFAOYSA-N methyl 7-methoxy-2h-indazole-3-carboxylate Chemical compound COC1=CC=CC2=C(C(=O)OC)NN=C21 QHDUJTCUPWHNPK-UHFFFAOYSA-N 0.000 description 2
- 230000004118 muscle contraction Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
- XXSQJWQCFIRWNW-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)-2,3-dihydro-1h-inden-5-amine Chemical compound C1C2=CC(N)=CC=C2CC1C1=CNC=N1 XXSQJWQCFIRWNW-UHFFFAOYSA-N 0.000 description 1
- PRPKJGGEZMASQX-UHFFFAOYSA-N 5-(2,3-dihydro-1h-inden-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2CC1C1=CNC=N1 PRPKJGGEZMASQX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
- 108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000491 multivariate analysis Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000003936 working memory Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939312669A GB9312669D0 (en) | 1993-06-18 | 1993-06-18 | New opticla isomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU211271A9 true HU211271A9 (en) | 1995-11-28 |
Family
ID=10737432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU95P/P00421P HU211271A9 (en) | 1993-06-18 | 1995-06-23 | New optical isomers |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0703903A1 (zh) |
| JP (1) | JPH08511554A (zh) |
| CN (1) | CN1125439A (zh) |
| AU (1) | AU6972594A (zh) |
| BG (1) | BG100218A (zh) |
| CA (1) | CA2165459A1 (zh) |
| CZ (1) | CZ332195A3 (zh) |
| EE (1) | EE9400010A (zh) |
| GB (1) | GB9312669D0 (zh) |
| HU (1) | HU211271A9 (zh) |
| IL (1) | IL109984A0 (zh) |
| LT (1) | LT3468B (zh) |
| LV (1) | LV11462B (zh) |
| NO (1) | NO955056D0 (zh) |
| NZ (1) | NZ267427A (zh) |
| PL (1) | PL312194A1 (zh) |
| SK (1) | SK157095A3 (zh) |
| WO (1) | WO1995000492A1 (zh) |
| ZA (1) | ZA944346B (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6613907B2 (en) | 2000-11-08 | 2003-09-02 | Amr Technology, Inc. | Process for the production of piperidine derivatives with microorganisms |
| FR2839719B1 (fr) * | 2002-05-16 | 2004-08-06 | Pf Medicament | Nouveaux composes imidazoliques, leur procede de preparation et leur utilisation a titre de medicaments |
| US8188126B2 (en) | 2002-05-16 | 2012-05-29 | Pierre Fabre Medicament | Imidazolic compounds and use thereof as alpha-2 adrenergic receptors |
| GB0226076D0 (en) * | 2002-11-08 | 2002-12-18 | Rp Scherer Technologies Inc | Improved formulations containing substituted imidazole derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2167408B (en) | 1984-11-23 | 1988-05-25 | Farmos Oy | Substituted imidazole derivatives and their preparation and use |
| FI81092C (fi) | 1986-05-15 | 1990-09-10 | Farmos Oy | Foerfarande foer framstaellning av terapeutiskt aktiva 4(5)-(2,3-dihydro-1h-inden-2-yl)-imidazolderivat. |
| GB2225782A (en) | 1988-12-09 | 1990-06-13 | Farmos Group Limited | Imidazole derivatives useful for treatment of diabetes |
| GB2244431A (en) | 1990-05-31 | 1991-12-04 | Farmos Oy | Treatment of age related memory impairment and other cognitive disorders |
| GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
-
1993
- 1993-06-18 GB GB939312669A patent/GB9312669D0/en active Pending
-
1994
- 1994-06-10 IL IL10998494A patent/IL109984A0/xx unknown
- 1994-06-15 EE EE9400010A patent/EE9400010A/xx unknown
- 1994-06-16 SK SK1570-95A patent/SK157095A3/sk unknown
- 1994-06-16 CA CA002165459A patent/CA2165459A1/en not_active Abandoned
- 1994-06-16 NZ NZ267427A patent/NZ267427A/en unknown
- 1994-06-16 PL PL94312194A patent/PL312194A1/xx unknown
- 1994-06-16 JP JP7502468A patent/JPH08511554A/ja active Pending
- 1994-06-16 CZ CZ953321A patent/CZ332195A3/cs unknown
- 1994-06-16 WO PCT/FI1994/000263 patent/WO1995000492A1/en not_active Application Discontinuation
- 1994-06-16 CN CN94192476A patent/CN1125439A/zh active Pending
- 1994-06-16 AU AU69725/94A patent/AU6972594A/en not_active Abandoned
- 1994-06-16 EP EP94918395A patent/EP0703903A1/en not_active Withdrawn
- 1994-06-17 LT LTIP1959A patent/LT3468B/lt not_active IP Right Cessation
- 1994-06-17 ZA ZA944346A patent/ZA944346B/xx unknown
-
1995
- 1995-06-23 HU HU95P/P00421P patent/HU211271A9/hu unknown
- 1995-12-13 NO NO955056A patent/NO955056D0/no unknown
- 1995-12-13 BG BG100218A patent/BG100218A/bg unknown
- 1995-12-19 LV LVP-95-376A patent/LV11462B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA944346B (en) | 1995-02-15 |
| EP0703903A1 (en) | 1996-04-03 |
| NO955056L (no) | 1995-12-13 |
| AU6972594A (en) | 1995-01-17 |
| NO955056D0 (no) | 1995-12-13 |
| BG100218A (bg) | 1996-06-28 |
| LV11462B (en) | 1996-12-20 |
| CZ332195A3 (en) | 1996-05-15 |
| IL109984A0 (en) | 1994-12-29 |
| EE9400010A (et) | 1995-12-15 |
| PL312194A1 (en) | 1996-04-01 |
| CA2165459A1 (en) | 1995-01-05 |
| LT3468B (en) | 1995-10-25 |
| GB9312669D0 (en) | 1993-08-04 |
| SK157095A3 (en) | 1996-06-05 |
| NZ267427A (en) | 1996-10-28 |
| LTIP1959A (en) | 1995-01-31 |
| JPH08511554A (ja) | 1996-12-03 |
| CN1125439A (zh) | 1996-06-26 |
| WO1995000492A1 (en) | 1995-01-05 |
| LV11462A (lv) | 1996-08-20 |
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