PH26127A - N-(pyridinyl)-1H-indol-1-amines and a process for their preparation - Google Patents

N-(pyridinyl)-1H-indol-1-amines and a process for their preparation Download PDF

Info

Publication number: PH26127A
Authority: PH; Philippines
Prior art keywords: loweralkyl; compound; formula; hydrogen; indol
Prior art date: 1987-04-24

Application number

PH36833A

Other languages

English (en)

Inventor

Richard Charles Effland

Joseph Thomas Klein

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.)

1987-04-24

Filing date

1988-04-22

Publication date

1992-02-24

1988-04-22 Application filed filed Critical

1992-02-24 Publication of PH26127A publication Critical patent/PH26127A/en

Links

238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 10
230000008569 process Effects 0.000 title claims abstract description 4
JULKLMOOTJHVHH-UHFFFAOYSA-N n-pyridin-2-ylindol-1-amine Chemical class C1=CC2=CC=CC=C2N1NC1=CC=CC=N1 JULKLMOOTJHVHH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 121
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 86
-1 hydroxy, nitro, amino Chemical group 0.000 claims abstract description 45
239000001257 hydrogen Substances 0.000 claims abstract description 35
150000002431 hydrogen Chemical group 0.000 claims abstract description 25
229910052736 halogen Inorganic materials 0.000 claims abstract description 23
150000002367 halogens Chemical group 0.000 claims abstract description 23
125000003118 aryl group Chemical group 0.000 claims abstract description 21
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 9
125000003435 aroyl group Chemical group 0.000 claims abstract description 8
125000001589 carboacyl group Chemical group 0.000 claims abstract description 8
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000005100 aryl amino carbonyl group Chemical group 0.000 claims abstract description 5
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
125000005239 aroylamino group Chemical group 0.000 claims abstract description 4
229910052799 carbon Inorganic materials 0.000 claims description 46
239000000203 mixture Substances 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 5
239000012948 isocyanate Substances 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
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125000001309 chloro group Chemical group Cl* 0.000 claims description 4
150000002513 isocyanates Chemical class 0.000 claims description 4
YFXZWVUZIPQSKX-UHFFFAOYSA-N n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1NC1=CC=NC=C1 YFXZWVUZIPQSKX-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Chemical group 0.000 claims description 3
229910052731 fluorine Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
OTPPJICEBWOCKD-UHFFFAOYSA-N besipirdine Chemical compound C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 OTPPJICEBWOCKD-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
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239000000935 antidepressant agent Substances 0.000 abstract description 6
125000001072 heteroaryl group Chemical group 0.000 abstract description 5
125000005129 aryl carbonyl group Chemical group 0.000 abstract description 4
125000006501 nitrophenyl group Chemical group 0.000 abstract description 4
229910052717 sulfur Inorganic materials 0.000 abstract description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract description 3
239000000730 antalgic agent Substances 0.000 abstract description 3
125000004802 cyanophenyl group Chemical group 0.000 abstract description 3
230000002708 enhancing effect Effects 0.000 abstract description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract 1
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238000004458 analytical method Methods 0.000 description 26
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MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 7
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206010015995 Eyelid ptosis Diseases 0.000 description 6
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CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 5
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125000001041 indolyl group Chemical group 0.000 description 5
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229930000680 A04AD01 - Scopolamine Natural products 0.000 description 4
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CGFBQVYTBDDHBS-UHFFFAOYSA-N 5-bromo-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(Br)=CC=C2N1NC1=CC=NC=C1 CGFBQVYTBDDHBS-UHFFFAOYSA-N 0.000 description 3
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AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 3
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TWBAZCSQSDRRLC-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-3-methylindol-1-amine Chemical compound C12=CC=CC=C2C(C)=CN1NC1=CC=NC=C1F TWBAZCSQSDRRLC-UHFFFAOYSA-N 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
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
230000001473 noxious effect Effects 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
150000002913 oxalic acids Chemical class 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
229960005301 pentazocine Drugs 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 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
150000003870 salicylic acids Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000012216 screening 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
230000035945 sensitivity Effects 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
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 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
238000010998 test method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- 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
- A61P25/24—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, ***e
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

PH36833A 1987-04-24 1988-04-22 N-(pyridinyl)-1H-indol-1-amines and a process for their preparation PH26127A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4207987A	1987-04-24	1987-04-24

Publications (1)

Publication Number	Publication Date
PH26127A true PH26127A (en)	1992-02-24

Family

ID=21919923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH36833A PH26127A (en)	1987-04-24	1988-04-22	N-(pyridinyl)-1H-indol-1-amines and a process for their preparation

Country Status (17)

Country	Link
EP (1)	EP0287982B1 (de)
JP (1)	JP2683360B2 (de)
KR (1)	KR960015003B1 (de)
AT (1)	ATE115143T1 (de)
AU (1)	AU594876B2 (de)
CA (1)	CA1330661C (de)
DE (1)	DE3852335T2 (de)
DK (1)	DK172153B1 (de)
ES (1)	ES2065324T3 (de)
FI (1)	FI90978C (de)
IE (1)	IE65349B1 (de)
IL (1)	IL86154A (de)
NO (1)	NO168104C (de)
NZ (1)	NZ224338A (de)
PH (1)	PH26127A (de)
PT (1)	PT87308B (de)
ZA (1)	ZA882810B (de)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4868190A (en) *	1988-12-27	1989-09-19	Hoechst-Roussel Pharmaceuticals, Inc.	N-pyridinyl-9H-carbazol-9-amines
US4983615A (en) *	1989-06-28	1991-01-08	Hoechst-Roussel Pharmaceuticals Inc.	Heteroarylamino- and heteroaryloxypyridinamine compounds which are useful in treating skin disorders
US5179119A (en) *	1989-08-02	1993-01-12	Hoechst-Roussel Pharmaceuticals Incorporated	1,3-dihydro-1-(pyridinylamino)-2H-indol-1-ones and intermediates for the preparation thereof
ATE118002T1 (de) *	1989-08-02	1995-02-15	Hoechst Roussel Pharma	2,3-dihydro-1-(pyridinylamino)-indole, verfahren zu ihrer herstellung und ihre anwendung als arzneimittel.
US5006537A (en) *	1989-08-02	1991-04-09	Hoechst-Roussel Pharmaceuticals, Inc.	1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones
US5179099A (en) *	1989-08-02	1993-01-12	Hoechst-Roussel Pharmaceuticals Incorporated	2,3-dihydro-1-(pyridinylamino)-indoles
US4983608A (en) *	1989-09-05	1991-01-08	Hoechst-Roussell Pharmaceuticals, Inc.	N-substituted-4-pyrimidinamines and pyrimidinediamines
US5102891A (en) *	1990-07-23	1992-04-07	Hoechst-Roussel Pharmaceuticals Inc.	1-(substituted pyridinylamino)-1H-indol-5-yl substituted carbamates
US5214038A (en) *	1991-04-15	1993-05-25	Hoechst-Roussel Pharmaceuticals Inc.	1-(pyrido[3,4-b]-1,4-oxazinyl-4-yl)-1H-indoles and intermediates for the preparation thereof
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
US5459274A (en) *	1994-05-13	1995-10-17	Hoechst-Roussel Pharmaceuticals Inc.	Preparation of N-alkyl-N-pyridinyl-1H-indol-1-amines
HUP9802413A3 (en) *	1995-07-27	2002-02-28	Aventis Pharmaceuticals Inc Br	Use of n-(pyrrol-1-yl)pyridinamines as anticonvulsant agents and for the preparation of a pharmaceutical composition for the treatment of convulsions
EP0840609B1 (de) *	1995-07-27	2002-06-05	Aventis Pharmaceuticals Inc.	Verwendung von substituierten und nichtsubstituierten n-(pyrrol-1-yl)pyridinaminen als antikonvulsiva
WO1998029407A2 (en) *	1996-12-27	1998-07-09	Hoechst Marion Roussel, Inc.	N-(pyridinylamino)isoindolines for treating alzheimer's and depression
EP1035114B1 (de) *	1999-03-10	2004-11-24	Tosoh Corporation	Verfahren zur Herstellung Stickstoffheterocyclischer Verbindungen
JP4779185B2 (ja) *	1999-03-10	2011-09-28	東ソー株式会社	含窒素複素環化合物及びその製造方法
JP4683166B2 (ja) *	1999-03-10	2011-05-11	東ソー株式会社	含窒素複素環化合物の製造方法
GB0119435D0 (en) *	2001-02-15	2001-10-03	Aventis Pharm Prod Inc	Method of treating of demyelinating diseases or conditions
US7538227B2 (en)	2004-01-13	2009-05-26	Sanofi-Aventis Deutschland Gmbh	Process for stabilizing 4-halopyridines
GT200500063A (es) *	2004-04-01	2005-10-14		Metodo para tratar la esquizofrenia y/o anormalidades glucoregulatorias
FR2888238B1 (fr) *	2005-07-07	2007-09-07	Servier Lab	Nouveaux derives 1h-indole-pyridinecarboxamides et 1h-indole-piperidinecarboxamide, leur procede de preparation et les compositions pharceumatiques qui les contiennent.
FR2911780A1 (fr) *	2007-01-26	2008-08-01	Urogene	Traitement de l'incontinence fecale.
JP5412422B2 (ja) *	2007-04-13	2014-02-12	サノフイ	Ｎ−アミノインドールの遷移金属触媒合成

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3242185A (en) *	1963-10-07	1966-03-22	Merck & Co Inc	Lower aliphatic acids, salts and derivatives thereof
DE1670184A1 (de) *	1967-01-20	1971-01-21	Boehringer Sohn Ingelheim	Verfahren zur Herstellung heterocyclisch substituierter Hydrazino-imidazoline-(2)
CH603581A5 (de) *	1974-03-29	1978-08-31	Siegfried Ag
US4260767A (en) *	1979-12-26	1981-04-07	American Cyanamid Company	2-Pyridylhydrazides
JPS60142955A (ja) *	1983-12-28	1985-07-29	Fuji Photo Film Co Ltd	インド−ル誘導体の製造方法
US4792562A (en) *	1985-12-04	1988-12-20	Hoechst-Roussel Pharmaceuticals, Inc.	N-(pyrrol-1-yl)pyridinamines having memory enhancing activity

1988
- 1988-04-18 AT AT88106121T patent/ATE115143T1/de not_active IP Right Cessation
- 1988-04-18 ES ES88106121T patent/ES2065324T3/es not_active Expired - Lifetime
- 1988-04-18 EP EP88106121A patent/EP0287982B1/de not_active Expired - Lifetime
- 1988-04-18 DE DE3852335T patent/DE3852335T2/de not_active Expired - Lifetime
- 1988-04-21 ZA ZA882810A patent/ZA882810B/xx unknown
- 1988-04-21 FI FI881874A patent/FI90978C/fi not_active IP Right Cessation
- 1988-04-22 JP JP63098467A patent/JP2683360B2/ja not_active Expired - Lifetime
- 1988-04-22 DK DK223488A patent/DK172153B1/da not_active IP Right Cessation
- 1988-04-22 AU AU15100/88A patent/AU594876B2/en not_active Expired
- 1988-04-22 PT PT87308A patent/PT87308B/pt not_active IP Right Cessation
- 1988-04-22 PH PH36833A patent/PH26127A/en unknown
- 1988-04-22 NZ NZ224338A patent/NZ224338A/en unknown
- 1988-04-22 CA CA000564923A patent/CA1330661C/en not_active Expired - Lifetime
- 1988-04-22 IL IL86154A patent/IL86154A/xx not_active IP Right Cessation
- 1988-04-22 IE IE121388A patent/IE65349B1/en not_active IP Right Cessation
- 1988-04-22 NO NO881776A patent/NO168104C/no not_active IP Right Cessation
- 1988-04-23 KR KR1019880004605A patent/KR960015003B1/ko not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0287982A2 (de)	1988-10-26
NO168104B (no)	1991-10-07
ES2065324T3 (es)	1995-02-16
PT87308B (pt)	1992-08-31
NO881776L (no)	1988-10-25
KR880012591A (ko)	1988-11-28
JPS63280079A (ja)	1988-11-17
AU594876B2 (en)	1990-03-15
JP2683360B2 (ja)	1997-11-26
DK223488A (da)	1988-10-25
NO881776D0 (no)	1988-04-22
CA1330661C (en)	1994-07-12
IE881213L (en)	1988-10-24
IL86154A (en)	1992-03-29
KR960015003B1 (ko)	1996-10-23
NZ224338A (en)	1991-07-26
DK223488D0 (da)	1988-04-22
NO168104C (no)	1992-01-15
FI881874A0 (fi)	1988-04-21
FI90978B (fi)	1994-01-14
DE3852335T2 (de)	1995-05-11
IE65349B1 (en)	1995-10-18
FI881874A (fi)	1988-10-25
DK172153B1 (da)	1997-12-01
AU1510088A (en)	1988-10-27
PT87308A (pt)	1988-05-01
ATE115143T1 (de)	1994-12-15
EP0287982A3 (de)	1991-03-27
FI90978C (fi)	1994-04-25
ZA882810B (en)	1988-10-20
IL86154A0 (en)	1988-11-15
DE3852335D1 (de)	1995-01-19
EP0287982B1 (de)	1994-12-07

Publication	Publication Date	Title
PH26127A (en)	1992-02-24	N-(pyridinyl)-1H-indol-1-amines and a process for their preparation
JP4086663B2 (ja)	2008-05-14	新規なスピロ三環式誘導体及びホスホジエステラーゼ７阻害剤としてのそれらの使用
KR900007780B1 (ko)	1990-10-20	축합된 피롤리논 유도체의 제조방법
KR102449652B1 (ko)	2022-09-29	Rock의 억제제로서의 스피로-융합 시클릭 우레아
AU669520B2 (en)	1996-06-13	Pyrido(2,3-d)pyrimidine derivatives as phosphodiesterase inhibitors
US4492702A (en)	1985-01-08	1-Phenyl-1,8-naphthridin-2(1H)-ones
IE50682B1 (en)	1986-06-11	Imidazo(1,2-a)pyridines,process for their preparation and pharmaceutical compositions containing them
NO894228L (no)	1989-10-24	Tienopyridiner, fremstilling, mellomprodukter og farmasoeytiske preparater.
US4970218A (en)	1990-11-13	N-(pyridinyl)-1H-indol-1-amines
EP0934319B1 (de)	2002-06-05	1H-PYRIDO[3,4-b]INDOLCARBOXAMIDDERIVATE, IHRE HERSTELLUNG UND THERAPEUTISCHE VERWENDUNG
JPH0568474B2 (de)	1993-09-29
US4880822A (en)	1989-11-14	N-(pyridinyl)-1H-indol-1-amines
US5066803A (en)	1991-11-19	2- and 3-aminomethyl-6-arylcarbonyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazines
US4628055A (en)	1986-12-09	Method for treating allergic reactions and compositions therefore
US5652245A (en)	1997-07-29	Heterocyclic amines having central nervous system activity
PT90907B (pt)	1994-12-30	Processo para a preparacao de novas 4,5,7,8-tetra-hidro-6h-tiazolo {5,4-d} azepinas e de composicoes farmaceuticas que as contem
EP0376155B1 (de)	1992-08-05	N-Pyridinyl-9H-carbazol-9-amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente
KR100248643B1 (ko)	2000-07-01	아릴 및 헤테로아릴 알콕시나프탈렌 유도체
EP0244201B1 (de)	1990-09-26	3-Hydroxypyridine
AU613137B2 (en)	1991-07-25	Pyrazol- and indazolpyridin amines, a process for their preparation and their use as medicaments
JP2807633B2 (ja)	1998-10-08	Ｎ−（ピリジニル）−ｉｈ−インドール−１−アミンを含有する強迫疾患治療剤
SK197A3 (en)	1997-06-04	Imidazopyridine-azolidinones, preparation method thereof, pharmaceutical composition containing same and their use
US5109135A (en)	1992-04-28	2- or 3-aminomethyl-4-amino-3,4-dihydro-2H-1,4-benzoxazine intermediates
KR900004831B1 (ko)	1990-07-07	폴리시클릭퀴놀린, 나프티리딘 및 피라지노피리딘 유도체
US5039811A (en)	1991-08-13	Preparation of N-(pyridinyl)-1H-indol-1-amines