SK281980B6 - Kryštallický (+)l-hydrogenvínan, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a jeho použitie - Google Patents
Kryštallický (+)l-hydrogenvínan, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a jeho použitie Download PDFInfo
- Publication number
- SK281980B6 SK281980B6 SK1520-95A SK152095A SK281980B6 SK 281980 B6 SK281980 B6 SK 281980B6 SK 152095 A SK152095 A SK 152095A SK 281980 B6 SK281980 B6 SK 281980B6
- Authority
- SK
- Slovakia
- Prior art keywords
- thiadiazol
- hexyloxy
- methylpyridine
- tetrahydro
- crystalline
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 239000003085 diluting agent Substances 0.000 claims abstract description 4
- 239000003937 drug carrier Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 239000006186 oral dosage form Substances 0.000 claims abstract 3
- -1 4-hexyloxy-1,2,5-thiadiazol-3-yl Chemical group 0.000 claims abstract 2
- JOLJIIDDOBNFHW-UHFFFAOYSA-N xanomeline Chemical compound CCCCCCOC1=NSN=C1C1=CCCN(C)C1 JOLJIIDDOBNFHW-UHFFFAOYSA-N 0.000 claims description 9
- 238000001953 recrystallisation Methods 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- 238000005185 salting out Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229940095064 tartrate Drugs 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PLDTVIHYDHJMEQ-UHFFFAOYSA-M 3-hexoxy-4-(1-methylpyridin-1-ium-3-yl)-1,2,5-thiadiazole;iodide Chemical compound [I-].CCCCCCOC1=NSN=C1C1=CC=C[N+](C)=C1 PLDTVIHYDHJMEQ-UHFFFAOYSA-M 0.000 description 1
- 229940127436 Cholinergic Muscarinic Agonists Drugs 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Compounds Of Unknown Constitution (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7257293A | 1993-06-04 | 1993-06-04 | |
| PCT/DK1994/000205 WO1994029303A1 (en) | 1993-06-04 | 1994-05-26 | Heterocyclic chemistry |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK152095A3 SK152095A3 (en) | 1996-10-02 |
| SK281980B6 true SK281980B6 (sk) | 2001-09-11 |
Family
ID=22108479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1520-95A SK281980B6 (sk) | 1993-06-04 | 1994-05-26 | Kryštallický (+)l-hydrogenvínan, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a jeho použitie |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5834495A (xx) |
| EP (1) | EP0703915B1 (xx) |
| JP (1) | JP3190679B2 (xx) |
| KR (1) | KR100339115B1 (xx) |
| CN (1) | CN1064681C (xx) |
| AT (1) | ATE196631T1 (xx) |
| AU (1) | AU698673B2 (xx) |
| CA (1) | CA2164296C (xx) |
| CZ (1) | CZ290550B6 (xx) |
| DE (1) | DE69426021T2 (xx) |
| DK (1) | DK0703915T3 (xx) |
| ES (1) | ES2152315T3 (xx) |
| FI (1) | FI955829A0 (xx) |
| GR (1) | GR3035033T3 (xx) |
| HU (1) | HUT75038A (xx) |
| IL (1) | IL109866A (xx) |
| NO (1) | NO305560B1 (xx) |
| NZ (2) | NZ267062A (xx) |
| PT (1) | PT703915E (xx) |
| SK (1) | SK281980B6 (xx) |
| WO (1) | WO1994029303A1 (xx) |
| ZA (1) | ZA943904B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6117890A (en) * | 1996-08-01 | 2000-09-12 | Eli Lilly And Company | Method for treating bipolar disorder |
| US6043258A (en) * | 1996-08-01 | 2000-03-28 | Eli Lilly And Company | Method for treating disruptive behavior disorders with xanomeline |
| US6090829A (en) * | 1996-08-01 | 2000-07-18 | Eli Lilly And Company | Method for treating excessive aggression |
| EP0821956A1 (en) * | 1996-08-01 | 1998-02-04 | Eli Lilly And Company | Method for treating disruptive behavior disorders |
| EP0821954A1 (en) * | 1996-08-01 | 1998-02-04 | Eli Lilly And Company | Method for treating mental retardation |
| US6034108A (en) * | 1997-07-28 | 2000-03-07 | Eli Lilly And Company | Method for treating mental retardation |
| CA2978201A1 (en) * | 2015-03-06 | 2016-09-15 | Chase Pharmaceuticals Corporation | Use of oxybutynin transdermal formulations to reduce side effects associated with muscarinic agonists |
| CN115974863B (zh) * | 2021-10-14 | 2024-12-31 | 南京迈诺威医药科技有限公司 | 占诺美林衍生物的苹果酸盐、a晶型及其制备方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5043345A (en) * | 1989-02-22 | 1991-08-27 | Novo Nordisk A/S | Piperidine compounds and their preparation and use |
| US5260311A (en) * | 1989-02-22 | 1993-11-09 | Novo Nordisk A/S | Piperidine compounds and their use |
| US5264444A (en) * | 1989-02-22 | 1993-11-23 | Novo Nordisk A/S | Piperidine compounds and use |
-
1994
- 1994-05-26 DE DE69426021T patent/DE69426021T2/de not_active Expired - Fee Related
- 1994-05-26 DK DK94917567T patent/DK0703915T3/da active
- 1994-05-26 CZ CZ19953210A patent/CZ290550B6/cs not_active IP Right Cessation
- 1994-05-26 AT AT94917567T patent/ATE196631T1/de not_active IP Right Cessation
- 1994-05-26 AU AU69242/94A patent/AU698673B2/en not_active Ceased
- 1994-05-26 PT PT94917567T patent/PT703915E/pt unknown
- 1994-05-26 ES ES94917567T patent/ES2152315T3/es not_active Expired - Lifetime
- 1994-05-26 CA CA002164296A patent/CA2164296C/en not_active Expired - Fee Related
- 1994-05-26 EP EP94917567A patent/EP0703915B1/en not_active Expired - Lifetime
- 1994-05-26 HU HU9503453A patent/HUT75038A/hu unknown
- 1994-05-26 JP JP50120095A patent/JP3190679B2/ja not_active Expired - Fee Related
- 1994-05-26 KR KR1019950705467A patent/KR100339115B1/ko not_active IP Right Cessation
- 1994-05-26 NZ NZ267062A patent/NZ267062A/en unknown
- 1994-05-26 CN CN94192681A patent/CN1064681C/zh not_active Expired - Fee Related
- 1994-05-26 SK SK1520-95A patent/SK281980B6/sk unknown
- 1994-05-26 WO PCT/DK1994/000205 patent/WO1994029303A1/en active IP Right Grant
- 1994-06-02 IL IL10986694A patent/IL109866A/xx not_active IP Right Cessation
- 1994-06-03 ZA ZA943904A patent/ZA943904B/xx unknown
-
1995
- 1995-12-01 NO NO954892A patent/NO305560B1/no not_active IP Right Cessation
- 1995-12-04 FI FI955829A patent/FI955829A0/fi not_active Application Discontinuation
-
1996
- 1996-11-26 US US08/756,835 patent/US5834495A/en not_active Expired - Fee Related
-
1999
- 1999-07-09 NZ NZ336733A patent/NZ336733A/en unknown
-
2000
- 2000-12-12 GR GR20000402720T patent/GR3035033T3/el not_active IP Right Cessation
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