CS117192A3 - SUBSTITUTED 3-(PYRIDINYLAMINO)INDOLES AND BENZO/b/THIOPHENES, PROCESS OFPREPARING SAID COMPOUNDS AND THEIR USE AS MEDICAMENTS - Google Patents

SUBSTITUTED 3-(PYRIDINYLAMINO)INDOLES AND BENZO/b/THIOPHENES, PROCESS OFPREPARING SAID COMPOUNDS AND THEIR USE AS MEDICAMENTS Download PDF

Info

Publication number: CS117192A3
Authority: CS; Czechoslovakia
Prior art keywords: compound; lower alkyl; group; formula; amino
Prior art date: 1991-04-17

Application number

CS921171A

Other languages

Czech (cs)

English (en)

Inventor

Richard Charles Effland

Joseph Thomas Klein

Lawrence Leo Martin

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.)

1991-04-17

Filing date

1992-04-16

Publication date

1992-11-18

1992-04-16 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1992-11-18 Publication of CS117192A3 publication Critical patent/CS117192A3/cs

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 163
238000000034 method Methods 0.000 title claims description 27
230000008569 process Effects 0.000 title claims description 14
239000003814 drug Substances 0.000 title claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title 1
150000002475 indoles Chemical class 0.000 title 1
229930192474 thiophene Natural products 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 25
150000002431 hydrogen Chemical class 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
238000011282 treatment Methods 0.000 claims abstract description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 61
-1 4-pyrimidinylamino Chemical group 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 10
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
125000001246 bromo group Chemical group Br* 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
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229910021653 sulphate ion Inorganic materials 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
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229910052760 oxygen Inorganic materials 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 10
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 3
125000001153 fluoro group Chemical group F* 0.000 claims 2
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238000003556 assay Methods 0.000 description 17
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WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000009103 reabsorption Effects 0.000 description 1
238000001953 recrystallisation 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
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
108010006590 serotonin 5 receptor Proteins 0.000 description 1
239000000952 serotonin receptor agonist Substances 0.000 description 1
239000004208 shellac Substances 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
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
HDDNYFLPWFSBLN-ZSHCYNCHSA-N tropanyl 3,5-dimethylbenzoate Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C1=CC(C)=CC(C)=C1 HDDNYFLPWFSBLN-ZSHCYNCHSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 1
229960002791 zimeldine Drugs 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- 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
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

CS921171A 1991-04-17 1992-04-16 SUBSTITUTED 3-(PYRIDINYLAMINO)INDOLES AND BENZO/b/THIOPHENES, PROCESS OFPREPARING SAID COMPOUNDS AND THEIR USE AS MEDICAMENTS CS117192A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/688,964 US5177088A (en)	1991-04-17	1991-04-17	Substituted 3-(pyridinylamino)-indoles

Publications (1)

Publication Number	Publication Date
CS117192A3 true CS117192A3 (en)	1992-11-18

Family

ID=24766519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS921171A CS117192A3 (en)	1991-04-17	1992-04-16	SUBSTITUTED 3-(PYRIDINYLAMINO)INDOLES AND BENZO/b/THIOPHENES, PROCESS OFPREPARING SAID COMPOUNDS AND THEIR USE AS MEDICAMENTS

Country Status (25)

Country	Link
US (1)	US5177088A (pl)
EP (1)	EP0509402B1 (pl)
JP (1)	JP2617650B2 (pl)
KR (1)	KR100254027B1 (pl)
AT (1)	ATE161840T1 (pl)
AU (1)	AU655253B2 (pl)
BG (1)	BG61034B1 (pl)
CA (1)	CA2066332C (pl)
CS (1)	CS117192A3 (pl)
DE (1)	DE69223837T2 (pl)
DK (1)	DK0509402T3 (pl)
ES (1)	ES2111580T3 (pl)
FI (1)	FI105096B (pl)
GR (1)	GR3026317T3 (pl)
HU (1)	HU215113B (pl)
IE (1)	IE921235A1 (pl)
IL (1)	IL101599A (pl)
MX (1)	MX9201759A (pl)
NO (1)	NO180486C (pl)
NZ (1)	NZ242359A (pl)
PL (1)	PL168905B1 (pl)
RO (1)	RO109847B1 (pl)
RU (1)	RU2060254C1 (pl)
TW (1)	TW200477B (pl)
ZA (1)	ZA922807B (pl)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5264442A (en) *	1990-08-13	1993-11-23	Hoechst-Roussel Pharmaceuticals Incorporated	Carbamoyl-1-(pyridinylalkyl)-1H-indoles, indolines and related analogs
US5328920A (en) *	1991-04-17	1994-07-12	Hoechst-Roussel Pharmaceuticals Incorporated	Substituted (pyridinylamino)-indoles
US5185350A (en) *	1991-09-23	1993-02-09	Hoechst-Roussel Pharmaceuticals Incorporated	Substituted pyridinylamino-1h-indoles,1h-indazoles,2h-indazoles, benzo (b)thiophenes and 1,2-benzisothiazoles
US5356910A (en)	1993-07-19	1994-10-18	Hoechst-Roussel Pharmaceuticals Inc.	Use of N-(pyridinyl)-1H-indol-1-amines for the treatment of obsessive-compulsive disorder
HUP9802492A3 (en) *	1995-06-06	1999-10-28	Hoechst Marion Roussel Inc Cin	Benzisoxazole and indazole derivatives as antipsychotic agents, process for their preparation and pharmaceutical compositions containing the same
US5668154A (en) *	1995-06-06	1997-09-16	Hoechst Marion Roussel Inc.	Pyridiniminyl-1,2-benzisoxazoles and -benzisothiazoles
IL130642A0 (en) *	1996-12-27	2000-06-01	Hoechst Marion Roussel Ltd	N-(pyridinylamino)isoindolines and related compounds
US7253165B2 (en) *	1999-09-14	2007-08-07	Aventis Pharmaceuticals Inc.	Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists
US7091199B1 (en)	1999-09-14	2006-08-15	Aventis Pharmaceuticals Inc.	Thienoisoxazole phenoxy unsubstituted ethyl and propyl derivatives useful as d4 antagonists
US7125903B1 (en)	1999-09-14	2006-10-24	Aventis Pharmaceuticals Inc.	Thienoisoxazolyl-and thienylpyrrazolyl-phenoxy substituted propyl derivatives useful as D4 antagonists
EA200200356A1 (ru) *	1999-09-14	2002-10-31	Авентис Фармасьютикалз Инк.	Бензизоксазолил-, пиридоизоксазолил- и бензтиенилфеноксипроизводные, используемые в качестве антагонистов рецептора d4
DE10029371A1 (de) *	2000-06-20	2002-01-03	Merck Patent Gmbh	Heterocyclische Aminoalkylpyridinderivate als Psychopharmaka
GB0217920D0 (en) *	2002-04-23	2002-09-11	Aventis Pharm Prod Inc	Interleukin-4 Gene Expression inhibitors
DE602005020280D1 (de)	2004-06-01	2010-05-12	Hoffmann La Roche	3-amino-1-arylpropyl-indole als monoamin-wiederaufnahmehemmer
BRPI0619263A2 (pt) *	2005-11-30	2011-09-27	Hoffmann La Roche	indóis de 3-amino-1-arilpropila e indóis aza-substituìdos, métodos para prepará-los, composição farmacêutica e uso dos referidos indóis
EP2351737A1 (en) *	2005-11-30	2011-08-03	F. Hoffmann-La Roche AG	3-Amino-1-arylpropyl indoles and aza-substituted indoles
AU2006319233B9 (en)	2005-11-30	2011-09-29	F. Hoffmann-La Roche Ag	3-amino-2-arylpropyl azaindoles and uses thereof
WO2009088192A2 (ko) *	2008-01-04	2009-07-16	Lg Life Sciences Ltd.	세포, 조직 및 장기 보존 효과를 갖는 인돌 및 인다졸 유도체

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0049779B1 (en) *	1980-09-18	1984-10-31	Asahi Kasei Kogyo Kabushiki Kaisha	3-aminoindazole derivatives and process for preparation thereof
IE58370B1 (en) *	1985-04-10	1993-09-08	Lundbeck & Co As H	Indole derivatives
US4717658A (en) *	1985-12-03	1988-01-05	Miles Inc.	Gram negative bacteria screening method with horseshoe crab amebocyte lysate (LAL)
US4970218A (en) *	1987-04-24	1990-11-13	Hoechst-Roussel Pharmaceuticals Inc.	N-(pyridinyl)-1H-indol-1-amines
US4806554A (en) *	1988-01-11	1989-02-21	Hoechst-Roussel Pharmaceuticals, Inc.	Pyrazol and indazolpyridinamines
US4954502A (en) *	1988-06-10	1990-09-04	Bristol-Myers Squibb Company	1-indolyalkyl-4-(substituted-pyridinyl)piperazines
EP0402644B1 (en) *	1989-05-19	1995-08-16	Hoechst-Roussel Pharmaceuticals Incorporated	N-(aryloxyalkyl)heteroarylpiperidines and -heteroarylpiperazines,a process for their preparation and their use as medicaments
US4983615A (en) *	1989-06-28	1991-01-08	Hoechst-Roussel Pharmaceuticals Inc.	Heteroarylamino- and heteroaryloxypyridinamine compounds which are useful in treating skin disorders
US4954503A (en) *	1989-09-11	1990-09-04	Hoechst-Roussel Pharmaceuticals, Inc.	3-(1-substituted-4-piperazinyl)-1H-indazoles
CA2030051C (en) *	1989-11-17	2001-08-07	Haruhiko Kikuchi	Indole derivatives

1991
- 1991-04-17 US US07/688,964 patent/US5177088A/en not_active Expired - Lifetime
1992
- 1992-04-09 AT AT92106162T patent/ATE161840T1/de not_active IP Right Cessation
- 1992-04-09 DK DK92106162T patent/DK0509402T3/da active
- 1992-04-09 EP EP92106162A patent/EP0509402B1/en not_active Expired - Lifetime
- 1992-04-09 ES ES92106162T patent/ES2111580T3/es not_active Expired - Lifetime
- 1992-04-09 BG BG96202A patent/BG61034B1/bg unknown
- 1992-04-09 DE DE69223837T patent/DE69223837T2/de not_active Expired - Fee Related
- 1992-04-14 RO RO92-200519A patent/RO109847B1/ro unknown
- 1992-04-14 MX MX9201759A patent/MX9201759A/es unknown
- 1992-04-14 NZ NZ242359A patent/NZ242359A/en unknown
- 1992-04-15 FI FI921693A patent/FI105096B/fi active
- 1992-04-15 PL PL92294239A patent/PL168905B1/pl unknown
- 1992-04-15 NO NO921505A patent/NO180486C/no unknown
- 1992-04-15 IL IL10159992A patent/IL101599A/en not_active IP Right Cessation
- 1992-04-16 RU SU925011369A patent/RU2060254C1/ru active
- 1992-04-16 CA CA002066332A patent/CA2066332C/en not_active Expired - Fee Related
- 1992-04-16 HU HU9201297A patent/HU215113B/hu not_active IP Right Cessation
- 1992-04-16 KR KR1019920006338A patent/KR100254027B1/ko not_active Expired - Fee Related
- 1992-04-16 CS CS921171A patent/CS117192A3/cs unknown
- 1992-04-16 ZA ZA922807A patent/ZA922807B/xx unknown
- 1992-04-16 JP JP4096304A patent/JP2617650B2/ja not_active Expired - Fee Related
- 1992-04-16 IE IE123592A patent/IE921235A1/en not_active IP Right Cessation
- 1992-04-21 AU AU15121/92A patent/AU655253B2/en not_active Ceased
- 1992-04-24 TW TW081103218A patent/TW200477B/zh active
1998
- 1998-03-11 GR GR980400508T patent/GR3026317T3/el unknown

Also Published As

Publication number	Publication date
AU1512192A (en)	1992-10-22
FI921693A7 (fi)	1992-10-18
KR920019777A (ko)	1992-11-20
NO180486B (no)	1997-01-20
PL168905B1 (pl)	1996-05-31
IL101599A0 (en)	1992-12-30
GR3026317T3 (en)	1998-06-30
NO921505D0 (no)	1992-04-15
JP2617650B2 (ja)	1997-06-04
AU655253B2 (en)	1994-12-08
KR100254027B1 (ko)	2000-05-01
ATE161840T1 (de)	1998-01-15
EP0509402A1 (en)	1992-10-21
HU215113B (hu)	1998-12-28
NO180486C (no)	1997-04-30
MX9201759A (es)	1992-10-01
DK0509402T3 (da)	1998-09-07
EP0509402B1 (en)	1998-01-07
CA2066332C (en)	2003-07-29
RU2060254C1 (ru)	1996-05-20
NZ242359A (en)	1995-03-28
RO109847B1 (ro)	1995-06-30
DE69223837T2 (de)	1998-06-25
DE69223837D1 (de)	1998-02-12
HU9201297D0 (en)	1992-07-28
NO921505L (no)	1992-10-19
CA2066332A1 (en)	1992-10-18
HUT62572A (en)	1993-05-28
BG61034B1 (bg)	1996-09-30
IE921235A1 (en)	1992-10-21
BG96202A (bg)	1993-12-24
PL294239A1 (en)	1993-06-14
US5177088A (en)	1993-01-05
IL101599A (en)	1996-05-14
TW200477B (pl)	1993-02-21
FI921693A0 (fi)	1992-04-15
ZA922807B (en)	1992-11-25
ES2111580T3 (es)	1998-03-16
JPH05117266A (ja)	1993-05-14
FI105096B (fi)	2000-06-15

Publication	Publication Date	Title
CS117192A3 (en)	1992-11-18	SUBSTITUTED 3-(PYRIDINYLAMINO)INDOLES AND BENZO/b/THIOPHENES, PROCESS OFPREPARING SAID COMPOUNDS AND THEIR USE AS MEDICAMENTS
US5834493A (en)	1998-11-10	Indole derivatives as 5-HT1A and/or 5-HT2 ligands
JP3057109B2 (ja)	2000-06-26	新規インドール誘導体
Street et al.	1993	Synthesis and serotonergic activity of 5-(oxadiazolyl) tryptamines: potent agonists for 5-HT1D receptors
US7238696B2 (en)	2007-07-03	Heterocyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands
JP2009541461A (ja)	2009-11-26	５−ｈｔ６モジュレーターとしてのインドール
KR101107807B1 (ko)	2012-01-25	5-ｈｔ(5ａ) 수용체 길항제로서의 2-아미노퀴놀린
US6329366B1 (en)	2001-12-11	Pharmaceutical compounds
US5328920A (en)	1994-07-12	Substituted (pyridinylamino)-indoles
EP0534343B1 (en)	1997-11-19	Substituted pyridinylamino-1H-indoles, 1H-indazoles, 2H-indazoles, benzo(b) thiophenes and 1,2-benzisothiazoles, a process for their preparation and their use as medicaments
US5246947A (en)	1993-09-21	Substituted pyridinylamino-1,2-benzisothiazoles and their use for treating depression
US5229401A (en)	1993-07-20	Substituted pyridinylamino benzo[b]thiophene compounds
JPH09512025A (ja)	1997-12-02	５ｈｔ▲下２ｃ▼および５ｈｔ▲下２ｂ▼アンタゴニストとしての三環式誘導体
US6022880A (en)	2000-02-08	Substituted pyridylamino indoles
JP2002510675A (ja)	2002-04-09	うつ病治療用のｎ−アリールオキシエチル−インドリル−アルキルアミン（５−ｈｔ１ａ受容体活性薬）
EP1859798B1 (en)	2015-12-30	N-(2-arylethyl) benzylamines as antagonists of the 5-ht6 receptor
EP1068199B1 (en)	2002-11-13	N-aryloxyethyl-indoly-alkylamines for the treatment of depression
US6150533A (en)	2000-11-21	N-aryloxyethyl-indoly-alkylamines for the treatment of depression
JP2000517318A (ja)	2000-12-26	ドパミンｄ２作動薬としての４―アミノエトキシインドロン誘導体
MXPA00009808A (en)	2002-06-05	N-aryloxyethyl-indoly-alkylamines for the treatment of depression