IL93068A - 8,9-annelated-1,2,3,4-tetrahydro-BETA-carboline derivatives, their preparation and pharmaceutical compositions containing them - Google Patents

8,9-annelated-1,2,3,4-tetrahydro-BETA-carboline derivatives, their preparation and pharmaceutical compositions containing them

Info

Publication number: IL93068A
Authority: IL; Israel
Prior art keywords: atoms; group; straight; substituted; hydrogen
Prior art date: 1989-01-19

Application number

IL9306890A

Other languages

English (en)

Other versions

IL93068A0 (en

Original Assignee

Duphar Int Res

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.)

1989-01-19

Filing date

1990-01-16

Publication date

1994-04-12

1990-01-16 Application filed by Duphar Int Res filed Critical Duphar Int Res

1990-11-05 Publication of IL93068A0 publication Critical patent/IL93068A0/xx

1994-04-12 Publication of IL93068A publication Critical patent/IL93068A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
150000001875 compounds Chemical class 0.000 claims abstract description 35
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 8
230000003480 fibrinolytic effect Effects 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
125000004429 atom Chemical group 0.000 claims abstract description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
125000006413 ring segment Chemical group 0.000 claims abstract description 3
125000005366 cycloalkylthio group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
150000002431 hydrogen Chemical group 0.000 claims 3
229940099990 ogen Drugs 0.000 claims 1
150000002367 halogens Chemical group 0.000 abstract description 3
239000000651 prodrug Substances 0.000 abstract description 3
229940002612 prodrug Drugs 0.000 abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229940073584 methylene chloride Drugs 0.000 description 7
208000007536 Thrombosis Diseases 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
-1 for example Chemical compound 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
ASLUVGUEPYXPRF-UHFFFAOYSA-N 1h-1-benzazonine Chemical compound N1C=CC=CC=CC2=CC=CC=C21 ASLUVGUEPYXPRF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
102000003978 Tissue Plasminogen Activator Human genes 0.000 description 2
108090000373 Tissue Plasminogen Activator Proteins 0.000 description 2
239000002253 acid Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
229960000187 tissue plasminogen activator Drugs 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
LOLJNNQHTPVJJR-UHFFFAOYSA-N 1-benzazecine Chemical compound N1=CC=CC=CC=CC2=CC=CC=C21 LOLJNNQHTPVJJR-UHFFFAOYSA-N 0.000 description 1
AVQSBCUVZLVLTM-UHFFFAOYSA-N 2,3,4,5,6,7-hexahydro-1h-1-benzazonine Chemical compound N1CCCCCCC2=CC=CC=C21 AVQSBCUVZLVLTM-UHFFFAOYSA-N 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
238000006407 Bischler-Napieralski reaction Methods 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
108010049003 Fibrinogen Proteins 0.000 description 1
102000008946 Fibrinogen Human genes 0.000 description 1
208000032843 Hemorrhage Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
241000700159 Rattus Species 0.000 description 1
238000006085 Schmidt reaction Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
108090000190 Thrombin Proteins 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229960000510 ammonia Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
208000034158 bleeding Diseases 0.000 description 1
231100000319 bleeding Toxicity 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229940012952 fibrinogen Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000023597 hemostasis Effects 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL9306890A 1989-01-19 1990-01-16 8,9-annelated-1,2,3,4-tetrahydro-BETA-carboline derivatives, their preparation and pharmaceutical compositions containing them IL93068A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL8900120		1989-01-19

Publications (2)

Publication Number	Publication Date
IL93068A0 IL93068A0 (en)	1990-11-05
IL93068A true IL93068A (en)	1994-04-12

Family

ID=19853980

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9306890A IL93068A (en)	1989-01-19	1990-01-16	8,9-annelated-1,2,3,4-tetrahydro-BETA-carboline derivatives, their preparation and pharmaceutical compositions containing them

Country Status (8)

Country	Link
US (1)	US5066649A (ja)
EP (1)	EP0380155A1 (ja)
JP (1)	JPH02233682A (ja)
AU (1)	AU635517B2 (ja)
CA (1)	CA2007815A1 (ja)
IL (1)	IL93068A (ja)
NZ (1)	NZ232121A (ja)
ZA (1)	ZA90301B (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0377238A1 (en) *	1988-12-22	1990-07-11	Duphar International Research B.V	New annelated indolo (3,2-c)-lactams
CA2140722A1 (en) *	1994-01-24	1995-07-25	Joseph A. Jakubowski	Beta-carboline thromboxane synthase inhibitors
US5550118A (en) *	1994-01-31	1996-08-27	Eli Lilly And Company	Polyhydronorharman synthase inhibitors

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3299078A (en) *	1962-10-01	1967-01-17	Smith Kline French Lab	Pyrido [3', 4': 4, 5] pyrrolo [3, 2, 1-hi] indoles and-[3, 2, 1-ij] quinolines
US3914421A (en) *	1972-06-19	1975-10-21	Endo Lab	Pyridopyrrolobenzheterocycles for combatting depression
EP0189612B1 (en) *	1984-12-21	1992-11-04	Duphar International Research B.V	New pharmaceutical compositions having a psychotropic activity
EP0190472B1 (en) *	1984-12-21	1989-07-12	Duphar International Research B.V	New pharmaceutical compositions having anti-psychotic properties
DE3855147D1 (de) *	1987-07-20	1996-05-02	Duphar Int Res	8,9-Anellierte 1,2,3,4-Tetrahydro-beta-carbolin-Derivate
DK686688A (da) *	1987-12-14	1989-06-15	Duphar Int Res	8,9-annelerede beta-carboliner, deres fremstilling og laegemidler indeholdende forbindelserne
EP0357122A3 (en) *	1988-08-29	1991-10-23	Duphar International Research B.V	Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties

1990
- 1990-01-15 EP EP90200091A patent/EP0380155A1/en not_active Ceased
- 1990-01-16 US US07/465,460 patent/US5066649A/en not_active Expired - Fee Related
- 1990-01-16 NZ NZ232121A patent/NZ232121A/en unknown
- 1990-01-16 CA CA002007815A patent/CA2007815A1/en not_active Abandoned
- 1990-01-16 IL IL9306890A patent/IL93068A/en not_active IP Right Cessation
- 1990-01-16 AU AU48510/90A patent/AU635517B2/en not_active Ceased
- 1990-01-16 ZA ZA90301A patent/ZA90301B/xx unknown
- 1990-01-18 JP JP2007250A patent/JPH02233682A/ja active Pending

Also Published As

Publication number	Publication date
CA2007815A1 (en)	1990-07-19
JPH02233682A (ja)	1990-09-17
NZ232121A (en)	1992-07-28
US5066649A (en)	1991-11-19
AU635517B2 (en)	1993-03-25
AU4851090A (en)	1990-07-26
EP0380155A1 (en)	1990-08-01
IL93068A0 (en)	1990-11-05
ZA90301B (en)	1991-03-27

Legal Events

Date	Code	Title	Description
1996-10-31	RH	Patent void

Publication	Publication Date	Title
KR100980163B1 (ko)	2010-09-03	데아자퓨린 및 이의 용도
CA1338189C (en)	1996-03-26	8,9-anellated-1,2,3,4-tetrahydro-.beta.-carboline derivatives
AU634534B2 (en)	1993-02-25	New 3-n substituted carbamoyl-indole derivatives
US5328905A (en)	1994-07-12	8,9-anellated-1,2,3,4-tetrahydro-β-carboline derivatives
AU716435B2 (en)	2000-02-24	Novel indole-2,3-dione-3-oxime derivatives
EP0109921A1 (en)	1984-05-30	Benzodiazepine receptors and their preparation
AU655634B2 (en)	1995-01-05	New active compounds
AU2004238329A1 (en)	2004-11-25	Cytotoxic indeno and isoindoloisoquinolones
WO2002004459A1 (en)	2002-01-17	Modulators of protein tyrosine phosphatases (ptpases)
JP2002504544A (ja)	2002-02-12	置換されたシクロアルキル−４−オキソニコチン酸カルボキシアミド；ｇａｂａ脳受容体リガンド
EP0197282A1 (en)	1986-10-15	Novel oxadiazolyl imidazobenzodiazepine derivatives and methods of preparing such compounds
EP0213499A2 (de)	1987-03-11	Aminosäure-Derivate, Verfahren zu ihrer Herstellung und Verwendung
CA1338190C (en)	1996-03-26	8,9-ANNELATED-ß-CARBOLINES AND 8,9-ANNELATED-3, 4-DIHYDRO-.BETA.-CAR BOLINES
HU192052B (en)	1987-05-28	Process for preparing new beta-carboline derivatives and pharmaceutical compositions containing them
IL93068A (en)	1994-04-12	8,9-annelated-1,2,3,4-tetrahydro-BETA-carboline derivatives, their preparation and pharmaceutical compositions containing them
US4748179A (en)	1988-05-31	β-carbolin-3-carboxylic acid derivatives and their use as benzodiazepine antagonists
AU621323B2 (en)	1992-03-12	8,9-annelated-beta-carbolines and 8,9-annelated-3,4-dihydro- beta-carbolines
US4843080A (en)	1989-06-27	1,12-disubstituted octahydroindolo[2,3-]quinolizine derivatives, pharmaceutical compositions
US4831035A (en)	1989-05-16	Substituted hexahydroarylquinolizines
FR2508457A1 (fr)	1982-12-31	Pyrrolo(2,1-b)quinazolines et pyrido(2,1-b)quinazolines substituees, leur preparation et leurs utilisations therapeutiques
US4305938A (en)	1981-12-15	2,8-Disubstituted-10-hydroxy-5,5-dimethyl-tetrahydro-and hexahydro-5H-[1]-benzopyrano[4,3-c]pyridines, compositions and use
US4492697A (en)	1985-01-08	4H-Imidazo[2,3-c]pyrido[2,3-e][1,4]oxazine derivatives
US4916223A (en)	1990-04-10	Substituted hexahydroarylquinolizines
HU189572B (en)	1986-07-28	Process for producing 6-substituted hexahydro-indazol-isoquinolines
DK151964B (da)	1988-01-18	Beta-carbolin-3-carboxylsyrederivater og fremgangsmaade til fremstilling af samme samt farmaceutisk praeparat