IL117795A - 6,7-דיהדרו-3- )2-ניטרופניל( 1, 2- בנזיסוקסאזול-h) 54(-אונים ומלחים מוספים המקובלים בתכשירים רפואיים - Google Patents
6,7-דיהדרו-3- )2-ניטרופניל( 1, 2- בנזיסוקסאזול-h) 54(-אונים ומלחים מוספים המקובלים בתכשירים רפואייםInfo
- Publication number
- IL117795A IL117795A IL117795A IL11779592A IL117795A IL 117795 A IL117795 A IL 117795A IL 117795 A IL117795 A IL 117795A IL 11779592 A IL11779592 A IL 11779592A IL 117795 A IL117795 A IL 117795A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- loweralkyl
- pharmaceutically acceptable
- addition salts
- nitrophenyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 4
- GEUUYJJWODKICD-UHFFFAOYSA-N 3-(2-nitrophenyl)-6,7-dihydro-5h-1,2-benzoxazol-4-one Chemical class [O-][N+](=O)C1=CC=CC=C1C1=NOC2=C1C(=O)CCC2 GEUUYJJWODKICD-UHFFFAOYSA-N 0.000 title claims description 4
- -1 loweralkyl Inorganic materials 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 230000003287 optical effect Effects 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 150000001204 N-oxides Chemical class 0.000 claims abstract 2
- 238000000034 method Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 230000007074 memory dysfunction Effects 0.000 abstract 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical class C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- HUIVMWSIMINFRO-UHFFFAOYSA-N n-chloro-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NCl HUIVMWSIMINFRO-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
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)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/654,691 US5210087A (en) | 1991-02-13 | 1991-02-13 | 9-aminotetrahydroacridines and related compounds |
| IL10092192A IL100921A (he) | 1991-02-13 | 1992-02-11 | 9- אמינוטטראהידרואקרידינדיאולים ותרכבות דומות תהליך להכנתם תרכבות ביניים שלהם ותכשירי רוקחות המכילים אותם |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL117795A true IL117795A (he) | 1998-01-04 |
Family
ID=24625869
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL117795A IL117795A (he) | 1991-02-13 | 1992-02-11 | 6,7-דיהדרו-3- )2-ניטרופניל( 1, 2- בנזיסוקסאזול-h) 54(-אונים ומלחים מוספים המקובלים בתכשירים רפואיים |
| IL10092192A IL100921A (he) | 1991-02-13 | 1992-02-11 | 9- אמינוטטראהידרואקרידינדיאולים ותרכבות דומות תהליך להכנתם תרכבות ביניים שלהם ותכשירי רוקחות המכילים אותם |
| IL11779596A IL117795A0 (en) | 1991-02-13 | 1996-04-02 | Dihydrobenzisoxazolines |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10092192A IL100921A (he) | 1991-02-13 | 1992-02-11 | 9- אמינוטטראהידרואקרידינדיאולים ותרכבות דומות תהליך להכנתם תרכבות ביניים שלהם ותכשירי רוקחות המכילים אותם |
| IL11779596A IL117795A0 (en) | 1991-02-13 | 1996-04-02 | Dihydrobenzisoxazolines |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US5210087A (he) |
| EP (1) | EP0499231B1 (he) |
| JP (1) | JPH07121915B2 (he) |
| KR (1) | KR100223132B1 (he) |
| AT (1) | ATE153331T1 (he) |
| AU (1) | AU664165B2 (he) |
| BR (1) | BR9200475A (he) |
| CA (1) | CA2061084A1 (he) |
| CZ (1) | CZ281927B6 (he) |
| DE (1) | DE69219801T2 (he) |
| DK (1) | DK0499231T3 (he) |
| ES (1) | ES2102417T3 (he) |
| FI (2) | FI96308C (he) |
| GR (1) | GR3024310T3 (he) |
| HU (1) | HU219451B (he) |
| IE (1) | IE920459A1 (he) |
| IL (3) | IL117795A (he) |
| MX (1) | MX9200607A (he) |
| NO (1) | NO177933C (he) |
| NZ (3) | NZ241586A (he) |
| PL (6) | PL168153B1 (he) |
| RO (1) | RO112354B1 (he) |
| RU (1) | RU2083564C1 (he) |
| TW (1) | TW221426B (he) |
| ZA (1) | ZA921004B (he) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210087A (en) * | 1991-02-13 | 1993-05-11 | Hoechst-Roussel Pharmaceuticals Inc. | 9-aminotetrahydroacridines and related compounds |
| ES2059263B1 (es) * | 1992-10-27 | 1995-10-01 | Vita Invest Sa | Procedimiento para la obtencion del (+)-9-amino-1,2,3,4-tetrahidroacridin-1-ol. |
| US5434170A (en) * | 1993-12-23 | 1995-07-18 | Andrulis Pharmaceuticals Corp. | Method for treating neurocognitive disorders |
| ES2144353B1 (es) * | 1997-12-26 | 2001-01-01 | Consejo Superior Investigacion | Nuevos analogos de tacrina: potenciales agentes neuroprotectores para las enfermedades de alzheimer y parkinson. su procedimiento de obtencion. |
| EP1484325B1 (en) | 2002-03-08 | 2014-06-18 | Japan Science and Technology Agency | Isoxazole derivatives and process for producing the same |
| RU2616247C1 (ru) * | 2016-03-28 | 2017-04-13 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Северо-Осетинский государственный университет имени Коста Левановича Хетагурова" (СОГУ) | Твердая лекарственная форма, обладающая холинопозитивным действием, на основе 9-бутиламино-3,3-диметил-1,2,4-тригидроакридина |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232945A (en) * | 1962-08-13 | 1966-02-01 | S E Massengill Company | 7,8,9,10-tetrahalo-6h-cyclohepta-(b)-quinolines |
| EP0179383B1 (en) * | 1984-10-25 | 1991-05-29 | Hoechst-Roussel Pharmaceuticals Incorporated | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds, a process for their preparation and their use as medicaments |
| US4631286A (en) * | 1984-10-25 | 1986-12-23 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| US4695573A (en) * | 1984-10-25 | 1987-09-22 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| IL87861A0 (en) * | 1987-10-05 | 1989-03-31 | Pfizer | 4-aminopyridine derivatives |
| MX13270A (es) * | 1987-10-05 | 1993-06-01 | Pfizer | Procedimiento para la preparacion de derivados de 4-aminopiridina |
| GB8827704D0 (en) * | 1988-11-28 | 1988-12-29 | Fujisawa Pharmaceutical Co | New acridine derivatives & processes for their production |
| US5441727A (en) * | 1989-06-21 | 1995-08-15 | The Procter & Gamble Company | Diketone deodorant composition and method of deodorization |
| US5053513A (en) * | 1990-03-29 | 1991-10-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of reducing a carbonyl containing acridine |
| US5210087A (en) * | 1991-02-13 | 1993-05-11 | Hoechst-Roussel Pharmaceuticals Inc. | 9-aminotetrahydroacridines and related compounds |
| GB2264707A (en) * | 1991-06-18 | 1993-09-08 | Roger Michael Marchbanks | Acridine derivatives for treating alzheimer's disease |
-
1991
- 1991-02-13 US US07/654,691 patent/US5210087A/en not_active Expired - Fee Related
-
1992
- 1992-01-30 TW TW081100687A patent/TW221426B/zh active
- 1992-02-10 RO RO92-200124A patent/RO112354B1/ro unknown
- 1992-02-11 IL IL117795A patent/IL117795A/he not_active IP Right Cessation
- 1992-02-11 NZ NZ241586A patent/NZ241586A/en unknown
- 1992-02-11 NZ NZ260694A patent/NZ260694A/en unknown
- 1992-02-11 FI FI920566A patent/FI96308C/fi active
- 1992-02-11 NZ NZ270647A patent/NZ270647A/en unknown
- 1992-02-11 IL IL10092192A patent/IL100921A/he not_active IP Right Cessation
- 1992-02-12 AU AU10903/92A patent/AU664165B2/en not_active Ceased
- 1992-02-12 PL PL92296319A patent/PL168153B1/pl unknown
- 1992-02-12 JP JP4024914A patent/JPH07121915B2/ja not_active Expired - Fee Related
- 1992-02-12 PL PL92293443A patent/PL169095B1/pl unknown
- 1992-02-12 KR KR1019920002007A patent/KR100223132B1/ko not_active IP Right Cessation
- 1992-02-12 NO NO920547A patent/NO177933C/no not_active IP Right Cessation
- 1992-02-12 ES ES92102332T patent/ES2102417T3/es not_active Expired - Lifetime
- 1992-02-12 AT AT92102332T patent/ATE153331T1/de not_active IP Right Cessation
- 1992-02-12 MX MX9200607A patent/MX9200607A/es not_active IP Right Cessation
- 1992-02-12 ZA ZA921004A patent/ZA921004B/xx unknown
- 1992-02-12 PL PL92308050A patent/PL168906B1/pl unknown
- 1992-02-12 HU HU9200423A patent/HU219451B/hu not_active IP Right Cessation
- 1992-02-12 PL PL92308048A patent/PL168862B1/pl unknown
- 1992-02-12 BR BR929200475A patent/BR9200475A/pt not_active Application Discontinuation
- 1992-02-12 DK DK92102332.1T patent/DK0499231T3/da active
- 1992-02-12 IE IE045992A patent/IE920459A1/en not_active IP Right Cessation
- 1992-02-12 DE DE69219801T patent/DE69219801T2/de not_active Expired - Fee Related
- 1992-02-12 CA CA002061084A patent/CA2061084A1/en not_active Abandoned
- 1992-02-12 PL PL92308049A patent/PL168861B1/pl unknown
- 1992-02-12 RU SU5010876/04A patent/RU2083564C1/ru not_active IP Right Cessation
- 1992-02-12 PL PL92296320A patent/PL166939B1/pl unknown
- 1992-02-12 EP EP92102332A patent/EP0499231B1/en not_active Expired - Lifetime
- 1992-02-12 CZ CS92426A patent/CZ281927B6/cs unknown
-
1993
- 1993-03-01 US US08/024,037 patent/US5382594A/en not_active Expired - Fee Related
-
1994
- 1994-12-13 FI FI945854A patent/FI97056C/fi active
-
1995
- 1995-05-31 US US08/451,327 patent/US5502203A/en not_active Expired - Fee Related
-
1996
- 1996-04-02 IL IL11779596A patent/IL117795A0/xx unknown
-
1997
- 1997-07-30 GR GR970401959T patent/GR3024310T3/el unknown
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