LV10189B - TETRAHYDROISOQUINOLINYLCARBAMATES OF 1,2,3,3a,8,8a-HEXAHYDRO-1,3a,8-TRIMETHYLPYROLO£2,3-b|INDOLE - Google Patents

TETRAHYDROISOQUINOLINYLCARBAMATES OF 1,2,3,3a,8,8a-HEXAHYDRO-1,3a,8-TRIMETHYLPYROLO£2,3-b|INDOLE Download PDF

Info

Publication number: LV10189B
Authority: LV; Latvia
Prior art keywords: cis; compound; trimethylpyrrolo; carbamate; tetrahydroisoquinolinyl
Prior art date: 1990-06-27

Application number

LVP-93-575A

Other languages

English (en)

Latvian (lv)

Other versions

LV10189A (lv

Inventor

Hamer Russell Richard Lee

Helsley Grover Cleveland

Glamkowski Edward Joseph

Chiang Yulin

Freed Brian Scott

Kurys Barbara Elaine

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.)

1990-06-27

Filing date

1993-06-15

Publication date

1995-08-20

1993-06-15 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1994-10-20 Publication of LV10189A publication Critical patent/LV10189A/xx

1995-08-20 Publication of LV10189B publication Critical patent/LV10189B/en

Links

SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 2
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150000001875 compounds Chemical class 0.000 claims abstract description 69
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150000002367 halogens Chemical class 0.000 claims abstract description 9
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LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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HKGWQUVGHPDEBZ-OLZOCXBDSA-N eseroline Chemical compound C1=C(O)C=C2[C@]3(C)CCN(C)[C@@H]3N(C)C2=C1 HKGWQUVGHPDEBZ-OLZOCXBDSA-N 0.000 claims description 3
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AVPBMJRCGOKTAK-UHFFFAOYSA-N (1-butyl-3,4-dihydro-2H-isoquinolin-1-yl) carbamate Chemical compound C(N)(OC1(NCCC2=CC=CC=C12)CCCC)=O AVPBMJRCGOKTAK-UHFFFAOYSA-N 0.000 claims 1
YPHDQIPQPJZMOC-UHFFFAOYSA-N (1-ethyl-3,4-dihydro-2H-isoquinolin-1-yl) carbamate Chemical compound CCC1(NCCc2ccccc12)OC(N)=O YPHDQIPQPJZMOC-UHFFFAOYSA-N 0.000 claims 1
QSQVEHZXDZFVNA-UHFFFAOYSA-N (1-methyl-3,4-dihydro-2h-isoquinolin-1-yl) carbamate Chemical compound C1=CC=C2C(C)(OC(N)=O)NCCC2=C1 QSQVEHZXDZFVNA-UHFFFAOYSA-N 0.000 claims 1
JDVBSILZRIPYMX-UHFFFAOYSA-N (1-propyl-3,4-dihydro-2H-isoquinolin-1-yl) carbamate Chemical compound CCCC1(NCCc2ccccc12)OC(N)=O JDVBSILZRIPYMX-UHFFFAOYSA-N 0.000 claims 1
NBBYXZQBIIWEEV-UHFFFAOYSA-N (6-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl) carbamate Chemical compound NC(=O)OC1NCCc2cc(Cl)ccc12 NBBYXZQBIIWEEV-UHFFFAOYSA-N 0.000 claims 1
JCUINAFDFPQJAZ-UHFFFAOYSA-N (6-chloro-1-methyl-3,4-dihydro-2h-isoquinolin-1-yl) carbamate Chemical compound ClC1=CC=C2C(C)(OC(N)=O)NCCC2=C1 JCUINAFDFPQJAZ-UHFFFAOYSA-N 0.000 claims 1
QEWBNBLPHZKVNW-UHFFFAOYSA-N (6-hydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl) carbamate Chemical compound OC1=CC=C2C(OC(=O)N)NCCC2=C1 QEWBNBLPHZKVNW-UHFFFAOYSA-N 0.000 claims 1
MLRITTDBWDGJNQ-UHFFFAOYSA-N (6-hydroxy-1-methyl-3,4-dihydro-2h-isoquinolin-1-yl) carbamate Chemical compound OC1=CC=C2C(C)(OC(N)=O)NCCC2=C1 MLRITTDBWDGJNQ-UHFFFAOYSA-N 0.000 claims 1
DSPRMTWPUKDLTN-UHFFFAOYSA-N (7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl) carbamate Chemical compound NC(=O)OC1NCCc2ccc(Cl)cc12 DSPRMTWPUKDLTN-UHFFFAOYSA-N 0.000 claims 1
OFVGEBIFDOILMQ-UHFFFAOYSA-N (7-chloro-1-methyl-3,4-dihydro-2h-isoquinolin-1-yl) carbamate Chemical compound C1=C(Cl)C=C2C(C)(OC(N)=O)NCCC2=C1 OFVGEBIFDOILMQ-UHFFFAOYSA-N 0.000 claims 1
WLKRXXLADKZOLU-UHFFFAOYSA-N (7-hydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl) carbamate Chemical compound C1=C(O)C=C2C(OC(=O)N)NCCC2=C1 WLKRXXLADKZOLU-UHFFFAOYSA-N 0.000 claims 1
KJCKKFFSJZFGBJ-UHFFFAOYSA-N (7-hydroxy-1-methyl-3,4-dihydro-2h-isoquinolin-1-yl) carbamate Chemical compound C1=C(O)C=C2C(C)(OC(N)=O)NCCC2=C1 KJCKKFFSJZFGBJ-UHFFFAOYSA-N 0.000 claims 1
IECNMUVOKOCCLQ-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-1-yl carbamate Chemical compound C1=CC=C2C(OC(=O)N)NCCC2=C1 IECNMUVOKOCCLQ-UHFFFAOYSA-N 0.000 claims 1
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
238000000576 coating method Methods 0.000 description 1
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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239000003550 marker Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
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STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
229940012189 methyl orange Drugs 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960001047 methyl salicylate 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
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000036473 myasthenia Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000000346 nonvolatile oil Substances 0.000 description 1
230000012154 norepinephrine uptake Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
229960003343 ouabain Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002913 oxalic acids Chemical class 0.000 description 1
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239000008188 pellet Substances 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
229960003418 phenoxybenzamine Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
YPDVTKJXVHYWFY-UHFFFAOYSA-N phosphoric acid;n'-propan-2-ylpyridine-4-carbohydrazide Chemical compound OP(O)(O)=O.CC(C)NNC(=O)C1=CC=NC=C1 YPDVTKJXVHYWFY-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
210000005241 right ventricle Anatomy 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
238000003345 scintillation counting Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-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)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Psychiatry (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)

LVP-93-575A 1990-06-27 1993-06-15 TETRAHYDROISOQUINOLINYLCARBAMATES OF 1,2,3,3a,8,8a-HEXAHYDRO-1,3a,8-TRIMETHYLPYROLO£2,3-b|INDOLE LV10189B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1990/003552 WO1992000072A1 (en)	1990-06-27	1990-06-27	Tetrahydroisoquinolinylcarbamates of 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

Publications (2)

Publication Number	Publication Date
LV10189A LV10189A (lv)	1994-10-20
LV10189B true LV10189B (en)	1995-08-20

Family

ID=22220922

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-93-575A LV10189B (en)	1990-06-27	1993-06-15	TETRAHYDROISOQUINOLINYLCARBAMATES OF 1,2,3,3a,8,8a-HEXAHYDRO-1,3a,8-TRIMETHYLPYROLO£2,3-b\|INDOLE

Country Status (18)

Country	Link
EP (1)	EP0538248B1 (lt)
KR (1)	KR0172971B1 (lt)
AT (1)	ATE163183T1 (lt)
AU (1)	AU649953B2 (lt)
BG (1)	BG61188B1 (lt)
DE (1)	DE69032046T2 (lt)
DK (1)	DK0538248T3 (lt)
ES (1)	ES2113859T3 (lt)
FI (1)	FI97229C (lt)
GE (1)	GEP19991747B (lt)
LT (1)	LT3598B (lt)
LV (1)	LV10189B (lt)
MC (1)	MC2287A1 (lt)
NO (1)	NO179910C (lt)
RO (1)	RO110501B1 (lt)
RU (1)	RU2124516C1 (lt)
SG (1)	SG70968A1 (lt)
WO (1)	WO1992000072A1 (lt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4791107A (en) *	1986-07-16	1988-12-13	Hoechst-Roussel Pharmaceuticals, Inc.	Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use
IT1271679B (it) *	1994-07-18	1997-06-04	Mediolanum Farmaceutici Srl	Derivati del fenilcarbammato atti all'impiego come anticolinesterasici
US5665880A (en) *	1996-10-31	1997-09-09	Hoechst Marion Roussel, Inc.	Method of preparation of physostigmine carbamate derivatives from eseretholes
US5677457A (en) *	1996-12-19	1997-10-14	Hoechst Marion Roussel, Inc.	Method of preparation of physostigmine carbamate derivatives from eseroline ethers
ATE264844T1 (de) *	1999-02-04	2004-05-15	Sk Corp	Tetrahydroisochinolinalkanol-derivate und diese enthaltende pharmazeutische zubereitungen

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU1547689A3 (ru) *	1984-10-18	1990-02-28	Щиба-Гейги Аг (Фирма)	Инсектицидное средство
US4791107A (en) *	1986-07-16	1988-12-13	Hoechst-Roussel Pharmaceuticals, Inc.	Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use
DK168069B1 (da) *	1987-11-11	1994-01-31	Hoffmann La Roche	Isoquinolinderivater og en fremgangsmaade til fremstilling af octahydroisoquinoliner ud fra derivaterne
US4914102A (en) *	1989-09-28	1990-04-03	Hoechst Roussel Pharmaceuticals, Inc.	N-aminocarbamates related to physostigmine, pharmacentical compositions and use
AU634380B2 (en) *	1990-05-17	1993-02-18	Hoechst-Roussel Pharmaceuticals Incorporated	Alpha-oxopyrrolo(2,3-b)indole acetic acids, esters, amides and related analogs, a process for their preparation and their use as medicaments
SU1746663A1 (ru) *	1990-06-26	1994-05-30	Институт Органической Химии Ан Усср	Метил-n-(n-перфторалкилтиофенил)карбаматы, обладающие свойствами регулятора роста растений, фунгицида, бактерицида

1990
- 1990-06-27 RU RU92016550A patent/RU2124516C1/ru active
- 1990-06-27 AT AT90910230T patent/ATE163183T1/de not_active IP Right Cessation
- 1990-06-27 MC MC90@@D patent/MC2287A1/xx unknown
- 1990-06-27 AU AU59313/90A patent/AU649953B2/en not_active Ceased
- 1990-06-27 DE DE69032046T patent/DE69032046T2/de not_active Expired - Fee Related
- 1990-06-27 WO PCT/US1990/003552 patent/WO1992000072A1/en not_active Ceased
- 1990-06-27 EP EP90910230A patent/EP0538248B1/en not_active Expired - Lifetime
- 1990-06-27 DK DK90910230T patent/DK0538248T3/da active
- 1990-06-27 SG SG1996003071A patent/SG70968A1/en unknown
- 1990-06-27 RO RO92-01561A patent/RO110501B1/ro unknown
- 1990-06-27 ES ES90910230T patent/ES2113859T3/es not_active Expired - Lifetime
- 1990-06-27 KR KR1019920703313A patent/KR0172971B1/ko not_active Expired - Fee Related
1992
- 1992-12-23 FI FI925872A patent/FI97229C/fi active
- 1992-12-23 NO NO925008A patent/NO179910C/no not_active IP Right Cessation
- 1992-12-23 BG BG97231A patent/BG61188B1/bg unknown
1993
- 1993-06-15 LV LVP-93-575A patent/LV10189B/en unknown
- 1993-07-29 GE GEAP19931278A patent/GEP19991747B/en unknown
- 1993-09-03 LT LTIP923A patent/LT3598B/lt not_active IP Right Cessation

Also Published As

Publication number	Publication date
BG97231A (bg)	1993-12-24
DE69032046D1 (de)	1998-03-19
NO925008D0 (no)	1992-12-23
EP0538248B1 (en)	1998-02-11
RU2124516C1 (ru)	1999-01-10
LT3598B (en)	1995-12-27
EP0538248A4 (lt)	1994-08-03
FI97229C (fi)	1996-11-11
AU649953B2 (en)	1994-06-09
LV10189A (lv)	1994-10-20
WO1992000072A1 (en)	1992-01-09
DE69032046T2 (de)	1998-08-27
BG61188B1 (bg)	1997-02-28
NO179910B (no)	1996-09-30
DK0538248T3 (da)	1998-09-23
FI925872L (fi)	1992-12-23
ATE163183T1 (de)	1998-02-15
FI925872A0 (fi)	1992-12-23
FI97229B (fi)	1996-07-31
EP0538248A1 (en)	1993-04-28
NO179910C (no)	1997-01-08
RO110501B1 (ro)	1996-01-30
SG70968A1 (en)	2000-03-21
ES2113859T3 (es)	1998-05-16
LTIP923A (en)	1995-03-27
GEP19991747B (en)	1999-09-10
NO925008L (no)	1992-12-23
MC2287A1 (fr)	1993-07-14
KR0172971B1 (ko)	1999-02-01
AU5931390A (en)	1992-01-23

Publication	Publication Date	Title
US4914102A (en)	1990-04-03	N-aminocarbamates related to physostigmine, pharmacentical compositions and use
IE64429B1 (en)	1995-08-09	1, 2, 3, 3a, 8, 8a-hexahydro-1, 3a, 8-trimethylpyrroloÚ2, 3-b¾ indoles, a process for their preparation and their use as medicaments
FI93451C (fi)	1995-04-10	Menetelmä terapeuttisesti käyttökelpoisten /(3aS-cis)-1,2,3,3a,8,8a-heksahydropyrrolo/2,3-b/indol-5-yyli/aminokarbonyyli/karbamaattijohdannaisten valmistamiseksi
JP2001508400A (ja)	2001-06-26	アセチルコリンエステラーゼ阻害剤および鎮痛剤としてのイサチン誘導体
EP0682947B1 (en)	1997-09-10	Medicament for therapeutic and prophylactic treatment of diseases caused by smooth muscle cell hyperplasia
JPS5910584A (ja)	1984-01-20	イミダゾリジン誘導体
LV10189B (en)	1995-08-20	TETRAHYDROISOQUINOLINYLCARBAMATES OF 1,2,3,3a,8,8a-HEXAHYDRO-1,3a,8-TRIMETHYLPYROLO£2,3-b\|INDOLE
JPH04264030A (ja)	1992-09-18	抗喘息剤
US5177101A (en)	1993-01-05	Memory enhancing and analgesic aminocarbonylcarbamates related to physostigmine
US5556862A (en)	1996-09-17	Pharmaceutical compositions containing isoquinoline derivatives
SK1912004A3 (en)	2004-09-08	Nicotinic acetylcholine receptor agonists in the treatment of restless legs syndrome
CA2085216C (en)	2000-12-05	Tetrahydroisoquinolinylcarbamates of 1,2,3,3a,8,8a- hexahydro-1,3a,8-trimethylpyrrolo ¬2,3-b\| indole
JPS60158190A (ja)	1985-08-19	ヒダントイン誘導体およびその製法ならびにそれを含有する医薬
US4621101A (en)	1986-11-04	Pharmaceutical compositions with antianginal activity
AU685820B2 (en)	1998-01-29	Tetrahydroisoquinolinylcarbamates of 1,2,3,3A,8,8A-hexahydro-1,3A,8-trimethylpyrrolo(2,3-B)indole
US5580877A (en)	1996-12-03	Pyrazolo-quinoline derivatives for treating cerebral ischemia
US4528290A (en)	1985-07-09	Stimulating dopamine D-1 receptors
JP3022959B2 (ja)	2000-03-21	アセチルコリンエステラーゼ阻害剤
JP2656998B2 (ja)	1997-09-24	１，２，３，３ａ，８，８ａ―ヘキサヒドロ―１，３ａ，８―トリメチルピロロ〔２，３―ｂ〕インドールのテトラヒドロイソキノリニルカルバメート
HU210179B (en)	1995-02-28	Process for preparing alfa-oxopyrrolo[2,3b]indole acetic acid, ester and amid derivatives and pharmaceutical compositions containing them as active ingredients
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