LT4417B - Nauji spiro [2h-1-benzopiran-2,4'-piperidin]-4(3h)-ono dariniai, jų adityvinės druskos su rūgštimis ir juos turinčios farmacinės kompozicijos - Google Patents
Nauji spiro [2h-1-benzopiran-2,4'-piperidin]-4(3h)-ono dariniai, jų adityvinės druskos su rūgštimis ir juos turinčios farmacinės kompozicijos Download PDFInfo
- Publication number
- LT4417B LT4417B LT97-193A LT97193A LT4417B LT 4417 B LT4417 B LT 4417B LT 97193 A LT97193 A LT 97193A LT 4417 B LT4417 B LT 4417B
- Authority
- LT
- Lithuania
- Prior art keywords
- formula
- benzopyran
- spiro
- piperidin
- halogen
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 38
- 239000002253 acid Substances 0.000 title claims abstract description 25
- QHNDQKSXDVVXIB-UHFFFAOYSA-N spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound O1C2=CC=CC=C2C(=O)CC21CCNCC2 QHNDQKSXDVVXIB-UHFFFAOYSA-N 0.000 title claims abstract description 19
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
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- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 238000003379 elimination reaction Methods 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 1
- 229960003404 mexiletine Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000011302 passive avoidance test Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006265 spirocyclization reaction Methods 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9600928A HUP9600928A3 (en) | 1996-04-10 | 1996-04-10 | Use of spiro[2h-1-benzopyran-2,4'-piperidin]-4(3h)-one derivatives for the preparation of pharmaceutical compositions treating dementia, novel derivatives and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT97193A LT97193A (en) | 1998-07-27 |
| LT4417B true LT4417B (lt) | 1998-12-28 |
Family
ID=89993875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT97-193A LT4417B (lt) | 1996-04-10 | 1997-12-10 | Nauji spiro [2h-1-benzopiran-2,4'-piperidin]-4(3h)-ono dariniai, jų adityvinės druskos su rūgštimis ir juos turinčios farmacinės kompozicijos |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6140336A (is) |
| EP (1) | EP0863904A2 (is) |
| JP (1) | JP3048068B2 (is) |
| KR (1) | KR19990022807A (is) |
| AU (1) | AU715104B2 (is) |
| BG (1) | BG102171A (is) |
| CA (1) | CA2224212A1 (is) |
| CZ (1) | CZ7698A3 (is) |
| EE (1) | EE9700334A (is) |
| FI (1) | FI974470A (is) |
| HU (1) | HUP9600928A3 (is) |
| ID (1) | ID16582A (is) |
| IL (1) | IL122542A (is) |
| IS (1) | IS4632A (is) |
| LT (1) | LT4417B (is) |
| LV (1) | LV12017B (is) |
| MD (1) | MD1837B2 (is) |
| NO (1) | NO975781L (is) |
| NZ (1) | NZ329359A (is) |
| PL (1) | PL327412A1 (is) |
| SI (1) | SI9720006A (is) |
| SK (1) | SK178697A3 (is) |
| TR (1) | TR199701627T1 (is) |
| WO (1) | WO1997037630A2 (is) |
| ZA (1) | ZA972905B (is) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI243173B (en) | 1999-11-17 | 2005-11-11 | Akzo Nobel Nv | Spiro[2H-1-benzopyran-2,4'-piperidine] derivatives |
| EP1716147B1 (en) * | 2004-01-08 | 2007-11-14 | F.Hoffmann-La Roche Ag | Diaza-spiropiperidine derivatives as inhibitors of glycine transporter 1 and glycine transporter 2 |
| WO2007088462A1 (en) * | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists of the h-3 receptor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0431943A2 (en) | 1989-12-08 | 1991-06-12 | Merck & Co. Inc. | Nitrogen-containing spirocycles |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2745306A1 (de) * | 1977-10-07 | 1979-04-19 | Bayer Ag | Insektizide mittel |
| JPS55143980A (en) * | 1979-04-27 | 1980-11-10 | Dai Ichi Seiyaku Co Ltd | Anti-allergic preparation |
-
1996
- 1996-04-10 HU HU9600928A patent/HUP9600928A3/hu unknown
-
1997
- 1997-04-03 CA CA002224212A patent/CA2224212A1/en not_active Abandoned
- 1997-04-03 WO PCT/HU1997/000012 patent/WO1997037630A2/en not_active Application Discontinuation
- 1997-04-03 NZ NZ329359A patent/NZ329359A/xx unknown
- 1997-04-03 JP JP9535989A patent/JP3048068B2/ja not_active Expired - Lifetime
- 1997-04-03 EP EP97914497A patent/EP0863904A2/en not_active Withdrawn
- 1997-04-03 CZ CZ9876A patent/CZ7698A3/cs unknown
- 1997-04-03 SK SK1786-97A patent/SK178697A3/sk unknown
- 1997-04-03 SI SI9720006A patent/SI9720006A/sl unknown
- 1997-04-03 IL IL12254297A patent/IL122542A/xx active IP Right Grant
- 1997-04-03 PL PL97327412A patent/PL327412A1/xx unknown
- 1997-04-03 EE EE9700334A patent/EE9700334A/xx unknown
- 1997-04-03 US US08/973,612 patent/US6140336A/en not_active Expired - Fee Related
- 1997-04-03 TR TR97/01627T patent/TR199701627T1/xx unknown
- 1997-04-03 MD MD98-0029A patent/MD1837B2/ro unknown
- 1997-04-03 KR KR1019970709276A patent/KR19990022807A/ko not_active Application Discontinuation
- 1997-04-03 AU AU21734/97A patent/AU715104B2/en not_active Ceased
- 1997-04-04 ZA ZA9702905A patent/ZA972905B/xx unknown
- 1997-04-10 ID IDP971182A patent/ID16582A/id unknown
- 1997-12-09 NO NO975781A patent/NO975781L/no not_active Application Discontinuation
- 1997-12-09 FI FI974470A patent/FI974470A/fi unknown
- 1997-12-09 IS IS4632A patent/IS4632A/is unknown
- 1997-12-10 LT LT97-193A patent/LT4417B/lt not_active IP Right Cessation
- 1997-12-24 LV LVP-97-253A patent/LV12017B/en unknown
-
1998
- 1998-01-09 BG BG102171A patent/BG102171A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0431943A2 (en) | 1989-12-08 | 1991-06-12 | Merck & Co. Inc. | Nitrogen-containing spirocycles |
Non-Patent Citations (3)
| Title |
|---|
| ELLIOTT JM ET AL.: "4-Oxospiro[benzopyran-2,4-piperidines] as class III antiarrhythmic agents. Pharmacological studies on 3,4-dihydro-1-[2-(benzofurazan-5-yl)- ethyl]-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4-piperidin]-4-on e (L-691,121)", J MED CHEM., 1992, pages 3973 |
| PRITCHETT DE, MERCHANT HE.: "The purification of hesperidin with formamide", J AM CHEM SOC., 1946, pages 2108 |
| YAMATO M, HASHIGAKI K, TSUTSUMI A, TASAKA K.: "Synthesis and structure-activity relationship of spiro[isochroman-piperidine] analogs for inhibition of histamine release. II.", CHEM PHARM BULL, 1981, pages 3494 - 3497 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 20010403 |