IL92420A - Fused heterocyclic derivatives of 1,2,3,4-tetrahydroacridine, a process for their preparation and pharmaceutical compositions containing them - Google Patents

Fused heterocyclic derivatives of 1,2,3,4-tetrahydroacridine, a process for their preparation and pharmaceutical compositions containing them

Info

Publication number: IL92420A
Authority: IL; Israel
Prior art keywords: compound; formula; hydrogen; loweralkyl; pharmaceutically acceptable
Prior art date: 1988-11-25

Application number

IL9242089A

Other languages

English (en)

Other versions

IL92420A0 (en

Inventor

Gregory M Shutske

Kevin J Kapples

Original Assignee

Hoechst Roussel Pharma

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-11-25

Filing date

1989-11-23

Publication date

1994-02-27

1989-11-23 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1990-07-26 Publication of IL92420A0 publication Critical patent/IL92420A0/xx

1994-02-27 Publication of IL92420A publication Critical patent/IL92420A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims abstract description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
125000000623 heterocyclic group Chemical group 0.000 title description 2
RXBYRTSOWREATF-UHFFFAOYSA-N tetrahydroacridine Natural products C1=CC=C2C=C(CCCC3)C3=NC2=C1 RXBYRTSOWREATF-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 54
239000002253 acid Substances 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
230000007074 memory dysfunction Effects 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
101100097467 Arabidopsis thaliana SYD gene Chemical group 0.000 claims abstract 3
101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Chemical group 0.000 claims abstract 3
239000003814 drug Substances 0.000 claims abstract 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
230000001713 cholinergic effect Effects 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 5
GOKUZEJXRWFFNL-UHFFFAOYSA-N 14-oxa-8,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,10,12,15-octaene Chemical compound C1=CC=C2OC=NC3=C2C1=NC1=CC=CC=C31 GOKUZEJXRWFFNL-UHFFFAOYSA-N 0.000 claims 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
CJBUKDOMILOKST-UHFFFAOYSA-N chembl96196 Chemical compound N=1C(C2=CC=CC=C2N=2)=C3C=2CCCC3NC=1C1=CC=CC=C1 CJBUKDOMILOKST-UHFFFAOYSA-N 0.000 claims 1
SJZMSTAIWFGFOK-UHFFFAOYSA-N chembl96406 Chemical compound C1=CC=C2C(N=C(NC3CCC4)C)=C3C4=NC2=C1 SJZMSTAIWFGFOK-UHFFFAOYSA-N 0.000 claims 1
230000006735 deficit Effects 0.000 claims 1
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 abstract description 3
230000003247 decreasing effect Effects 0.000 abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
208000024827 Alzheimer disease Diseases 0.000 abstract 1
230000006949 cholinergic function Effects 0.000 abstract 1
239000000203 mixture Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 3
STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
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 3
229960002646 scopolamine Drugs 0.000 description 3
102100033639 Acetylcholinesterase Human genes 0.000 description 2
108010022752 Acetylcholinesterase Proteins 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
206010048650 Cholinesterase inhibition Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
208000026139 Memory disease Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241001231783 Teira Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
229940022698 acetylcholinesterase Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 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
239000002775 capsule Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
238000004040 coloring Methods 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000002950 deficient Effects 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
206010027175 memory impairment Diseases 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229960001697 physostigmine Drugs 0.000 description 1
PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- 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)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Hydrogenated Pyridines (AREA)

IL9242089A 1988-11-25 1989-11-23 Fused heterocyclic derivatives of 1,2,3,4-tetrahydroacridine, a process for their preparation and pharmaceutical compositions containing them IL92420A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/276,259 US4927820A (en)	1988-11-25	1988-11-25	Fused heterocyclic derivatives of 1,2,3,4-tetrahydroacridine

Publications (2)

Publication Number	Publication Date
IL92420A0 IL92420A0 (en)	1990-07-26
IL92420A true IL92420A (en)	1994-02-27

Family

ID=23055896

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9242089A IL92420A (en)	1988-11-25	1989-11-23	Fused heterocyclic derivatives of 1,2,3,4-tetrahydroacridine, a process for their preparation and pharmaceutical compositions containing them

Country Status (18)

Country	Link
US (1)	US4927820A (de)
EP (1)	EP0370449B1 (de)
JP (1)	JPH085881B2 (de)
KR (1)	KR0143235B1 (de)
AT (1)	ATE104298T1 (de)
AU (1)	AU623452B2 (de)
CA (1)	CA2003837C (de)
DE (1)	DE68914600T2 (de)
DK (1)	DK592589A (de)
ES (1)	ES2051965T3 (de)
FI (1)	FI90871C (de)
HU (1)	HU203551B (de)
IE (1)	IE63120B1 (de)
IL (1)	IL92420A (de)
NO (1)	NO173783C (de)
NZ (1)	NZ231494A (de)
PT (1)	PT92389B (de)
ZA (1)	ZA898989B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4920117A (en) *	1989-06-09	1990-04-24	Hoechst-Roussel Pharmaceuticals Inc.	4,5,5a,6-tetrahydro-3H-isoxazolo(5,4,3-kl)acridines, pharmaceutical compositions and use
US4994452A (en) *	1989-11-28	1991-02-19	Hoechst-Roussel Pharmaceuticals Inc.	Hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepines and related compounds
US5112829A (en) *	1989-11-28	1992-05-12	Hoechst-Roussel Pharmaceuticals Inc.	Hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepines and related compounds
US5861398A (en) *	1996-08-26	1999-01-19	Alanex Corporation	Benzoperimidine-carboxylic acids and derivatives thereof
KR101709141B1 (ko)	2008-01-25	2017-02-22	브이티브이 테라퓨틱스 엘엘씨	ＴＮＦ-α 합성의 조절자 및 ＰＤＥ4 억제제로서 3고리 화합물
TWI908838B (zh)	2020-07-28	2025-12-21	美商Ｖｔｖ治療有限責任公司	喹啉衍生物的鹽酸鹽的結晶形式

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3582995D1 (de) *	1984-10-25	1991-07-04	Hoechst Roussel Pharma	9-amino-1,2,3,4-tetrahydroacridin-1-ol und verwandte verbindungen, verfahren zu ihrer herstellung und verwendung als arzneimittel.
US4695573A (en) *	1984-10-25	1987-09-22	Hoechst-Roussel Pharmaceuticals Inc.	9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds
WO1989002739A1 (en) *	1987-10-05	1989-04-06	Pfizer Inc.	4-aminopyridine derivatives
US4920117A (en) *	1989-06-09	1990-04-24	Hoechst-Roussel Pharmaceuticals Inc.	4,5,5a,6-tetrahydro-3H-isoxazolo(5,4,3-kl)acridines, pharmaceutical compositions and use

1988
- 1988-11-25 US US07/276,259 patent/US4927820A/en not_active Expired - Fee Related
1989
- 1989-11-21 EP EP89121488A patent/EP0370449B1/de not_active Expired - Lifetime
- 1989-11-21 DE DE68914600T patent/DE68914600T2/de not_active Expired - Fee Related
- 1989-11-21 ES ES89121488T patent/ES2051965T3/es not_active Expired - Lifetime
- 1989-11-21 AT AT89121488T patent/ATE104298T1/de not_active IP Right Cessation
- 1989-11-23 FI FI895605A patent/FI90871C/fi not_active IP Right Cessation
- 1989-11-23 KR KR1019890017024A patent/KR0143235B1/ko not_active Expired - Fee Related
- 1989-11-23 PT PT92389A patent/PT92389B/pt not_active IP Right Cessation
- 1989-11-23 NZ NZ231494A patent/NZ231494A/en unknown
- 1989-11-23 IL IL9242089A patent/IL92420A/en not_active IP Right Cessation
- 1989-11-24 HU HU896174A patent/HU203551B/hu not_active IP Right Cessation
- 1989-11-24 AU AU45480/89A patent/AU623452B2/en not_active Ceased
- 1989-11-24 CA CA002003837A patent/CA2003837C/en not_active Expired - Fee Related
- 1989-11-24 IE IE375889A patent/IE63120B1/en not_active IP Right Cessation
- 1989-11-24 DK DK592589A patent/DK592589A/da not_active Application Discontinuation
- 1989-11-24 NO NO894698A patent/NO173783C/no not_active IP Right Cessation
- 1989-11-24 ZA ZA898989A patent/ZA898989B/xx unknown
- 1989-11-24 JP JP1303465A patent/JPH085881B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HU896174D0 (en)	1990-02-28
KR0143235B1 (ko)	1998-07-15
ZA898989B (en)	1990-08-29
US4927820A (en)	1990-05-22
IL92420A0 (en)	1990-07-26
DE68914600D1 (de)	1994-05-19
AU4548089A (en)	1990-05-31
PT92389A (pt)	1990-05-31
FI90871C (fi)	1994-04-11
NO894698D0 (no)	1989-11-24
CA2003837C (en)	2000-01-18
AU623452B2 (en)	1992-05-14
HUT53107A (en)	1990-09-28
ES2051965T3 (es)	1994-07-01
IE63120B1 (en)	1995-03-22
PT92389B (pt)	1995-07-18
CA2003837A1 (en)	1990-05-25
EP0370449A1 (de)	1990-05-30
NO894698L (no)	1990-05-28
JPH085881B2 (ja)	1996-01-24
HU203551B (en)	1991-08-28
DK592589D0 (da)	1989-11-24
NO173783B (no)	1993-10-25
IE893758L (en)	1990-05-25
ATE104298T1 (de)	1994-04-15
DE68914600T2 (de)	1994-09-15
NO173783C (no)	1994-02-02
KR900007848A (ko)	1990-06-02
NZ231494A (en)	1992-04-28
FI895605A0 (fi)	1989-11-23
EP0370449B1 (de)	1994-04-13
DK592589A (da)	1990-05-26
FI90871B (fi)	1993-12-31
JPH02193996A (ja)	1990-07-31

Legal Events

Date	Code	Title
1997-11-20	HC	Change of name of proprietor(s)
2000-07-26	KB	Patent renewed
2000-08-31	KB	Patent renewed
2004-07-25	RH1	Patent not in force

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US6248750B1 (en)	2001-06-19	9-hydroxyamino tetrahydroacridine and related compounds
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