DK170168B1 - Pyridoindolderivater og fremgangsmåde til fremstilling deraf, farmaceutisk præparat der indeholder sådanne derivater og anvendelse af derivaterne til fremstilling af et præparat og som medikament - Google Patents

Pyridoindolderivater og fremgangsmåde til fremstilling deraf, farmaceutisk præparat der indeholder sådanne derivater og anvendelse af derivaterne til fremstilling af et præparat og som medikament Download PDF

Info

Publication number: DK170168B1
Authority: DK; Denmark
Prior art keywords: methyl; imidazol; lower alkyl; salt; compound
Prior art date: 1988-09-27

Application number

DK474089A

Other languages

Danish (da)

English (en)

Other versions

DK474089A (da

DK474089D0 (da

Inventor

Kiyotaka Ito

Masayuki Kato

Hisashi Takasugi

Original Assignee

Fujisawa Pharmaceutical Co

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.)

1988-09-27

Filing date

1989-09-26

Publication date

1995-06-06

1988-09-27 Priority claimed from GB888822646A external-priority patent/GB8822646D0/en

1989-02-10 Priority claimed from GB898903044A external-priority patent/GB8903044D0/en

1989-09-26 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1989-09-26 Publication of DK474089D0 publication Critical patent/DK474089D0/da

1990-03-28 Publication of DK474089A publication Critical patent/DK474089A/da

1995-06-06 Application granted granted Critical

1995-06-06 Publication of DK170168B1 publication Critical patent/DK170168B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 32
238000002360 preparation method Methods 0.000 title claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 title claims description 12
239000003814 drug Substances 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 68
150000003839 salts Chemical class 0.000 claims abstract description 66
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
231100000252 nontoxic Toxicity 0.000 claims abstract description 4
230000003000 nontoxic effect Effects 0.000 claims abstract description 4
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
-1 1H-imidazole -4-yl Chemical group 0.000 claims description 69
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
AEKQMJRJRAHOAP-UHFFFAOYSA-N 10-methyl-7-[(5-methyl-1h-imidazol-4-yl)methyl]-8,9-dihydro-7h-pyrido[1,2-a]indol-6-one Chemical group N1C=NC(CC2C(N3C4=CC=CC=C4C(C)=C3CC2)=O)=C1C AEKQMJRJRAHOAP-UHFFFAOYSA-N 0.000 claims description 9
206010047700 Vomiting Diseases 0.000 claims description 8
125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 7
230000008673 vomiting Effects 0.000 claims description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
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229910052757 nitrogen Inorganic materials 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 4
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125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
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238000006243 chemical reaction Methods 0.000 description 37
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238000001819 mass spectrum Methods 0.000 description 20
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238000003756 stirring Methods 0.000 description 18
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239000013078 crystal Substances 0.000 description 17
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238000001704 evaporation Methods 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
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ZXHIYWJYTQDWAK-UHFFFAOYSA-N 1,7-dihydroindol-6-one Chemical compound C1=CC(=O)CC2=C1C=CN2 ZXHIYWJYTQDWAK-UHFFFAOYSA-N 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
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239000003921 oil Substances 0.000 description 12
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239000000047 product Substances 0.000 description 12
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239000000706 filtrate Substances 0.000 description 11
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
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DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 5
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101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 4
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238000006460 hydrolysis reaction Methods 0.000 description 4
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238000001556 precipitation Methods 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
201000009032 substance abuse Diseases 0.000 description 1
231100000736 substance abuse Toxicity 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 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
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Saccharide Compounds (AREA)
Pyridine Compounds (AREA)
Cephalosporin Compounds (AREA)

DK474089A 1988-09-27 1989-09-26 Pyridoindolderivater og fremgangsmåde til fremstilling deraf, farmaceutisk præparat der indeholder sådanne derivater og anvendelse af derivaterne til fremstilling af et præparat og som medikament DK170168B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8822646		1988-09-27
GB888822646A GB8822646D0 (en)	1988-09-27	1988-09-27	Pyridoindole derivatives & processes for preparation thereof
GB898903044A GB8903044D0 (en)	1989-02-10	1989-02-10	Pyridoindole derivatives and processes for preparation thereof
GB8903044		1989-02-10

Publications (3)

Publication Number	Publication Date
DK474089D0 DK474089D0 (da)	1989-09-26
DK474089A DK474089A (da)	1990-03-28
DK170168B1 true DK170168B1 (da)	1995-06-06

Family

ID=26294446

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK474089A DK170168B1 (da)	1988-09-27	1989-09-26	Pyridoindolderivater og fremgangsmåde til fremstilling deraf, farmaceutisk præparat der indeholder sådanne derivater og anvendelse af derivaterne til fremstilling af et præparat og som medikament

Country Status (20)

Country	Link
US (1)	US5141945A (de)
EP (1)	EP0361317B1 (de)
JP (1)	JPH02117675A (de)
KR (1)	KR0143999B1 (de)
CN (1)	CN1024552C (de)
AT (1)	ATE120743T1 (de)
AU (1)	AU627221B2 (de)
CA (1)	CA1338474C (de)
DE (1)	DE68922053T2 (de)
DK (1)	DK170168B1 (de)
ES (1)	ES2070154T3 (de)
FI (1)	FI92200C (de)
GR (1)	GR3015713T3 (de)
HK (1)	HK102096A (de)
HU (2)	HU206209B (de)
IE (1)	IE67350B1 (de)
IL (1)	IL91756A (de)
NO (1)	NO172541C (de)
PT (1)	PT91795B (de)
RU (1)	RU2001915C1 (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5290785A (en) *	1988-09-27	1994-03-01	Fujisawa Pharmaceutical Co., Ltd.	Therapeutic agent for ischemic diseases
US5173493A (en) *	1988-09-27	1992-12-22	Fujisawa Pharmaceutical Company, Ltd.	Pyridoindole derivatives and processes for preparation thereof
GB9214184D0 (en) *	1992-07-03	1992-08-12	Smithkline Beecham Plc	Pharmaceuticals
EP0688216A1 (de) *	1993-03-08	1995-12-27	Fujisawa Pharmaceutical Co., Ltd.	Medikament zur behandlung und prävention von zerebrovaskulären erkrankungen
AU3354895A (en) *	1994-09-19	1996-04-09	Fujisawa Pharmaceutical Co., Ltd.	Novel medicinal use of 5ht3 antagonist
WO1997011074A1 (en) *	1995-09-22	1997-03-27	Fujisawa Pharmaceutical Co., Ltd.	Novel processes for producing pyridoindole derivatives
FR2869316B1 (fr) *	2004-04-21	2006-06-02	Sanofi Synthelabo	Derives de pyridoindolone substitues en -6, leur preparation et leur application en therapeutique.
EP4729123A2 (de)	2017-04-24	2026-04-22	Alto Neuroscience, Inc.	Zusammensetzungen mit pramipexol und einem 5ht3 antagonist zur verwendung bei der behandlung von depression
CN116003407B (zh) *	2022-12-27	2025-04-01	株洲千金药业股份有限公司	一种大规模生产唑吡坦的合成方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU88268I2 (de) *	1984-01-25	1994-02-03
GB8516083D0 (en) *	1985-06-25	1985-07-31	Glaxo Group Ltd	Heterocyclic compounds
GB8518743D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Heterocyclic compounds
GR871809B (en) *	1986-11-28	1988-03-07	Glaxo Group Ltd	Process for the preparation of tricyclic ketones

1989
- 1989-09-14 AU AU41406/89A patent/AU627221B2/en not_active Ceased
- 1989-09-19 IE IE299989A patent/IE67350B1/en not_active IP Right Cessation
- 1989-09-20 US US07/409,744 patent/US5141945A/en not_active Expired - Fee Related
- 1989-09-21 EP EP89117498A patent/EP0361317B1/de not_active Expired - Lifetime
- 1989-09-21 ES ES89117498T patent/ES2070154T3/es not_active Expired - Lifetime
- 1989-09-21 AT AT89117498T patent/ATE120743T1/de not_active IP Right Cessation
- 1989-09-21 DE DE68922053T patent/DE68922053T2/de not_active Expired - Fee Related
- 1989-09-24 IL IL91756A patent/IL91756A/xx not_active IP Right Cessation
- 1989-09-25 FI FI894506A patent/FI92200C/fi not_active IP Right Cessation
- 1989-09-25 CA CA000612855A patent/CA1338474C/en not_active Expired - Fee Related
- 1989-09-25 PT PT91795A patent/PT91795B/pt not_active IP Right Cessation
- 1989-09-26 DK DK474089A patent/DK170168B1/da not_active IP Right Cessation
- 1989-09-26 NO NO893820A patent/NO172541C/no unknown
- 1989-09-26 KR KR1019890013798A patent/KR0143999B1/ko not_active Expired - Fee Related
- 1989-09-26 RU SU894742106A patent/RU2001915C1/ru active
- 1989-09-26 HU HU895038A patent/HU206209B/hu not_active IP Right Cessation
- 1989-09-26 CN CN89107692A patent/CN1024552C/zh not_active Expired - Fee Related
- 1989-09-27 JP JP1252986A patent/JPH02117675A/ja active Granted
1995
- 1995-04-06 GR GR950400770T patent/GR3015713T3/el unknown
- 1995-06-22 HU HU95P/P00372P patent/HU211139A9/hu unknown
1996
- 1996-06-13 HK HK102096A patent/HK102096A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE892999L (en)	1990-03-27
FI894506A0 (fi)	1989-09-25
KR900004733A (ko)	1990-04-12
DE68922053D1 (de)	1995-05-11
FI92200C (fi)	1994-10-10
JPH02117675A (ja)	1990-05-02
HUT51623A (en)	1990-05-28
NO893820D0 (no)	1989-09-26
PT91795A (pt)	1990-03-30
ATE120743T1 (de)	1995-04-15
US5141945A (en)	1992-08-25
NO172541B (no)	1993-04-26
JPH054392B2 (de)	1993-01-19
AU627221B2 (en)	1992-08-20
HK102096A (en)	1996-06-21
RU2001915C1 (ru)	1993-10-30
CN1024552C (zh)	1994-05-18
HU206209B (en)	1992-09-28
PT91795B (pt)	1995-05-31
EP0361317B1 (de)	1995-04-05
IL91756A (en)	1993-07-08
EP0361317A3 (de)	1991-07-24
ES2070154T3 (es)	1995-06-01
AU4140689A (en)	1990-04-05
FI894506L (fi)	1990-03-28
DK474089A (da)	1990-03-28
CA1338474C (en)	1996-07-23
NO172541C (no)	1993-08-04
HU211139A9 (en)	1995-10-30
DE68922053T2 (de)	1995-08-10
DK474089D0 (da)	1989-09-26
NO893820L (no)	1990-03-28
CN1041594A (zh)	1990-04-25
KR0143999B1 (ko)	1998-07-15
GR3015713T3 (en)	1995-07-31
IL91756A0 (en)	1990-06-10
IE67350B1 (en)	1996-03-20
EP0361317A2 (de)	1990-04-04
FI92200B (fi)	1994-06-30

Legal Events

Date	Code	Title	Description
1995-06-06	B1	Patent granted (law 1993)
2000-05-15	PBP	Patent lapsed

Publication	Publication Date	Title
DK169675B1 (da)	1995-01-09	4-Imidazolylmethyltetrahydrocarbazoloner, fremgangsmåde til fremstilling deraf samt farmaceutiske præparater indeholdende forbindelserne
CZ404491A3 (en)	1993-04-14	Lactam derivatives
US20090318443A1 (en)	2009-12-24	Kinase inhibitors
DK170168B1 (da)	1995-06-06	Pyridoindolderivater og fremgangsmåde til fremstilling deraf, farmaceutisk præparat der indeholder sådanne derivater og anvendelse af derivaterne til fremstilling af et præparat og som medikament
CA3186348A1 (en)	2021-12-16	Spiro compounds as melanocortin 4 receptor antagonists and uses thereof
WO1994007891A1 (en)	1994-04-14	1-substituted oxindoles and azaoxindoles as novel cognition enhancers
JPH03200786A (ja)	1991-09-02	ラクタム誘導体
US5173493A (en)	1992-12-22	Pyridoindole derivatives and processes for preparation thereof
KATo et al.	1994	New 5-HT3 (Serotonin-3) Receptor Antagonists. I. Synthesis and Structure-Activity Relationships of Pyrido [1, 2-α] indoles
US5290785A (en)	1994-03-01	Therapeutic agent for ischemic diseases
EP0420086B1 (de)	1995-12-13	Pyrimidoindolderivate und Verfahren zu ihrer Herstellung
US5256780A (en)	1993-10-26	Pyrimidoindole derivatives and processes for preparation thereof
AU2023320660A1 (en)	2025-02-27	TGF-β INHIBITOR COMPOUND AND USE THEREOF
US5519132A (en)	1996-05-21	Pyridine compounds
JPWO1995011245A1 (ja)	1996-03-26	インドール誘導体