AP876A - Tetrahydroquinolines as NMDA antagonists. - Google Patents

Tetrahydroquinolines as NMDA antagonists. Download PDF

Info

Publication number: AP876A
Authority: AP; ARIPO
Prior art keywords: carboxylic acid; dichloro; phenylcarbamoylmethylene; quinoline; compound
Prior art date: 1995-09-29

Application number

APAP/P/1998/001212A

Other languages

English (en)

Other versions

AP9801212A0 (en

Inventor

Romano D-Fabio

Simone Giacobbe

Barbara Bertani

Original Assignee

Glaxo Wellcome Spa

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.)

1995-09-29

Filing date

1996-09-26

Publication date

2000-09-27

1995-09-29 Priority claimed from GBGB9519893.3A external-priority patent/GB9519893D0/en

1996-08-17 Priority claimed from GBGB9617306.7A external-priority patent/GB9617306D0/en

1996-09-26 Application filed by Glaxo Wellcome Spa filed Critical Glaxo Wellcome Spa

1998-03-31 Publication of AP9801212A0 publication Critical patent/AP9801212A0/xx

2000-09-27 Application granted granted Critical

2000-09-27 Publication of AP876A publication Critical patent/AP876A/en

Links

HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 title claims description 8
239000005557 antagonist Substances 0.000 title abstract description 6
150000003530 tetrahydroquinolines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 156
150000003839 salts Chemical class 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 22
150000002148 esters Chemical class 0.000 claims abstract description 16
230000002461 excitatory amino acid Effects 0.000 claims abstract description 7
239000003257 excitatory amino acid Substances 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
-1 hydroxy, methoxy, amino Chemical group 0.000 claims description 63
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 32
125000006239 protecting group Chemical group 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 13
150000002431 hydrogen Chemical group 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 10
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
OSJVTYVKQNOXPP-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)CCC2=C1 OSJVTYVKQNOXPP-UHFFFAOYSA-N 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
125000000547 substituted alkyl group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
101100295741 Gallus gallus COR4 gene Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
HLHLASMGVJKRCF-JXMROGBWSA-N (4e)-4-(2-anilino-2-oxoethylidene)-5,7-dichloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C12=C(Cl)C=C(Cl)C=C2NC(C(=O)O)C\C1=C/C(=O)NC1=CC=CC=C1 HLHLASMGVJKRCF-JXMROGBWSA-N 0.000 claims description 2
LNYJXORXZWTJDA-YRNVUSSQSA-N (4e)-4-[2-(4-acetamidoanilino)-2-oxoethylidene]-5,7-dichloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 LNYJXORXZWTJDA-YRNVUSSQSA-N 0.000 claims description 2
HHIBQUYGKUKOLR-RMKNXTFCSA-N (4e)-4-[2-(4-aminoanilino)-2-oxoethylidene]-5,7-dichloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(N)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 HHIBQUYGKUKOLR-RMKNXTFCSA-N 0.000 claims description 2
JARAYNYVRUCFAJ-NTEUORMPSA-N (4e)-4-[2-[4-(2-acetamidoethyl)anilino]-2-oxoethylidene]-5,7-dichloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(CCNC(=O)C)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 JARAYNYVRUCFAJ-NTEUORMPSA-N 0.000 claims description 2
MEJOLWFQFOZGKV-NTUHNPAUSA-N (4e)-4-[2-[4-(acetamidomethyl)anilino]-2-oxoethylidene]-5,7-dichloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(CNC(=O)C)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 MEJOLWFQFOZGKV-NTUHNPAUSA-N 0.000 claims description 2
JCCJCTNJPWOBID-IZZDOVSWSA-N (4e)-4-[2-[4-[(carbamoylamino)methyl]anilino]-2-oxoethylidene]-5,7-dichloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(CNC(=O)N)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 JCCJCTNJPWOBID-IZZDOVSWSA-N 0.000 claims description 2
YKHBUQGOUVHHQT-XNTDXEJSSA-N (4e)-5,7-dichloro-4-[2-[4-(morpholin-4-ylmethyl)anilino]-2-oxoethylidene]-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C12=C(Cl)C=C(Cl)C=C2NC(C(=O)O)C\C1=C/C(=O)NC(C=C1)=CC=C1CN1CCOCC1 YKHBUQGOUVHHQT-XNTDXEJSSA-N 0.000 claims description 2
OXWCBNKJFVARHS-RIYZIHGNSA-N (4e)-5,7-dichloro-4-[2-[4-[(2-methylpropanoylamino)methyl]anilino]-2-oxoethylidene]-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(CNC(=O)C(C)C)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 OXWCBNKJFVARHS-RIYZIHGNSA-N 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
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230000001225 therapeutic effect Effects 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
ZKGDXYGRYZYSFU-JXMROGBWSA-N (4e)-4-(2-anilino-2-oxoethylidene)-5,7-dibromo-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C12=C(Br)C=C(Br)C=C2NC(C(=O)O)C\C1=C/C(=O)NC1=CC=CC=C1 ZKGDXYGRYZYSFU-JXMROGBWSA-N 0.000 claims 1
BBWWOCJHBMIAOY-PKNBQFBNSA-N (4e)-4-(2-anilino-2-oxoethylidene)-7-chloro-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C12=CC=C(Cl)C=C2NC(C(=O)O)C\C1=C/C(=O)NC1=CC=CC=C1 BBWWOCJHBMIAOY-PKNBQFBNSA-N 0.000 claims 1
GGMUXXNYJBLWJJ-UKTHLTGXSA-N (4e)-5,7-dichloro-4-[2-[4-(3-methylbutanoylamino)anilino]-2-oxoethylidene]-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC(NC(=O)CC(C)C)=CC=C1NC(=O)\C=C/1C2=C(Cl)C=C(Cl)C=C2NC(C(O)=O)C\1 GGMUXXNYJBLWJJ-UKTHLTGXSA-N 0.000 claims 1
BSVFJXLOAIUPSE-UHFFFAOYSA-N 5,7-dichloro-4-[2-(3-chloroanilino)-2-oxoethylidene]-2,3-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C12=C(Cl)C=C(Cl)C=C2NC(C(=O)O)CC1=CC(=O)NC1=CC=CC(Cl)=C1 BSVFJXLOAIUPSE-UHFFFAOYSA-N 0.000 claims 1
101150047265 COR2 gene Proteins 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 130
239000000243 solution Substances 0.000 description 110
239000000543 intermediate Substances 0.000 description 107
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
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239000007787 solid Substances 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
239000012267 brine Substances 0.000 description 33
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
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QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
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LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
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UXWQXBSQQHAGMG-UHFFFAOYSA-N tert-butyl n-[(4-aminophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(N)C=C1 UXWQXBSQQHAGMG-UHFFFAOYSA-N 0.000 description 1
HOPALBZGTWDOTL-UHFFFAOYSA-N tert-butyl n-[2-(4-aminophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=C(N)C=C1 HOPALBZGTWDOTL-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- 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
- A61P25/24—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
- A61P25/28—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
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Virology (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Addiction (AREA)
Cardiology (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Otolaryngology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

APAP/P/1998/001212A 1995-09-29 1996-09-26 Tetrahydroquinolines as NMDA antagonists. AP876A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9519893.3A GB9519893D0 (en)	1995-09-29	1995-09-29	Heterocyclic compounds
GBGB9617306.7A GB9617306D0 (en)	1996-08-17	1996-08-17	Heterocyclic compounds
PCT/EP1996/004206 WO1997012870A1 (en)	1995-09-29	1996-09-26	Tetrahydroquinolines as nmda antagonists

Publications (2)

Publication Number	Publication Date
AP9801212A0 AP9801212A0 (en)	1998-03-31
AP876A true AP876A (en)	2000-09-27

Family

ID=26307841

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1998/001212A AP876A (en)	1995-09-29	1996-09-26	Tetrahydroquinolines as NMDA antagonists.

Country Status (28)

Country	Link
US (1)	US5977136A (pl)
EP (1)	EP0854867B1 (pl)
JP (1)	JP4108123B2 (pl)
KR (1)	KR100464895B1 (pl)
CN (1)	CN1130346C (pl)
AP (1)	AP876A (pl)
AR (1)	AR005233A1 (pl)
AT (1)	ATE221520T1 (pl)
AU (1)	AU708148B2 (pl)
BR (1)	BR9610733A (pl)
CA (1)	CA2232509A1 (pl)
CZ (1)	CZ292379B6 (pl)
DE (1)	DE69622731T2 (pl)
DK (1)	DK0854867T3 (pl)
EA (1)	EA000875B1 (pl)
ES (1)	ES2180799T3 (pl)
HU (1)	HUP9900040A3 (pl)
IL (1)	IL123322A0 (pl)
IS (1)	IS4677A (pl)
MX (1)	MX9801967A (pl)
NO (1)	NO310355B1 (pl)
NZ (1)	NZ319596A (pl)
PL (1)	PL186781B1 (pl)
PT (1)	PT854867E (pl)
SI (1)	SI0854867T1 (pl)
TR (1)	TR199800531T1 (pl)
TW (1)	TW460465B (pl)
WO (1)	WO1997012870A1 (pl)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9617305D0 (en)	1996-08-17	1996-09-25	Glaxo Wellcome Spa	Heterocyclic compounds
GB9706294D0 (en) *	1997-03-26	1997-05-14	Glaxo Wellcome Spa	Heterocyclic compound
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1996
- 1996-09-26 CZ CZ1998940A patent/CZ292379B6/cs not_active IP Right Cessation
- 1996-09-26 BR BR9610733A patent/BR9610733A/pt not_active IP Right Cessation
- 1996-09-26 PL PL96325966A patent/PL186781B1/pl not_active IP Right Cessation
- 1996-09-26 IL IL12332296A patent/IL123322A0/xx not_active IP Right Cessation
- 1996-09-26 AU AU72148/96A patent/AU708148B2/en not_active Ceased
- 1996-09-26 CA CA002232509A patent/CA2232509A1/en not_active Abandoned
- 1996-09-26 DK DK96933399T patent/DK0854867T3/da active
- 1996-09-26 US US09/029,860 patent/US5977136A/en not_active Expired - Fee Related
- 1996-09-26 NZ NZ319596A patent/NZ319596A/en not_active IP Right Cessation
- 1996-09-26 AT AT96933399T patent/ATE221520T1/de not_active IP Right Cessation
- 1996-09-26 PT PT96933399T patent/PT854867E/pt unknown
- 1996-09-26 ES ES96933399T patent/ES2180799T3/es not_active Expired - Lifetime
- 1996-09-26 SI SI9630523T patent/SI0854867T1/xx unknown
- 1996-09-26 DE DE69622731T patent/DE69622731T2/de not_active Expired - Lifetime
- 1996-09-26 EP EP96933399A patent/EP0854867B1/en not_active Expired - Lifetime
- 1996-09-26 HU HU9900040A patent/HUP9900040A3/hu unknown
- 1996-09-26 WO PCT/EP1996/004206 patent/WO1997012870A1/en not_active Ceased
- 1996-09-26 KR KR10-1998-0702321A patent/KR100464895B1/ko not_active Expired - Fee Related
- 1996-09-26 EA EA199800230A patent/EA000875B1/ru not_active IP Right Cessation
- 1996-09-26 TR TR1998/00531T patent/TR199800531T1/xx unknown
- 1996-09-26 AP APAP/P/1998/001212A patent/AP876A/en active
- 1996-09-26 JP JP51394797A patent/JP4108123B2/ja not_active Expired - Fee Related
- 1996-09-26 CN CN96198560A patent/CN1130346C/zh not_active Expired - Fee Related
- 1996-09-30 AR ARP960104543A patent/AR005233A1/es active IP Right Grant
- 1996-10-04 TW TW085112168A patent/TW460465B/zh not_active IP Right Cessation
1998
- 1998-02-27 IS IS4677A patent/IS4677A/is unknown
- 1998-03-12 MX MX9801967A patent/MX9801967A/es not_active IP Right Cessation
- 1998-03-27 NO NO19981396A patent/NO310355B1/no not_active IP Right Cessation

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Also Published As

Publication number	Publication date
MX9801967A (es)	1998-08-30
JPH11512728A (ja)	1999-11-02
BR9610733A (pt)	1999-07-13
JP4108123B2 (ja)	2008-06-25
KR100464895B1 (ko)	2005-05-16
NZ319596A (en)	1999-09-29
ATE221520T1 (de)	2002-08-15
DK0854867T3 (da)	2002-12-02
NO981396D0 (no)	1998-03-27
CA2232509A1 (en)	1997-04-10
PT854867E (pt)	2002-12-31
IL123322A0 (en)	1998-09-24
HUP9900040A3 (en)	2001-01-29
SI0854867T1 (en)	2003-02-28
EP0854867A1 (en)	1998-07-29
AU708148B2 (en)	1999-07-29
CZ94098A3 (cs)	1998-07-15
TW460465B (en)	2001-10-21
KR19990063850A (ko)	1999-07-26
IS4677A (is)	1998-02-27
AP9801212A0 (en)	1998-03-31
ES2180799T3 (es)	2003-02-16
WO1997012870A1 (en)	1997-04-10
CZ292379B6 (cs)	2003-09-17
NO310355B1 (no)	2001-06-25
US5977136A (en)	1999-11-02
PL325966A1 (en)	1998-08-17
EP0854867B1 (en)	2002-07-31
EA199800230A1 (ru)	1998-10-29
HUP9900040A2 (hu)	1999-04-28
PL186781B1 (pl)	2004-02-27
AU7214896A (en)	1997-04-28
TR199800531T1 (xx)	1998-06-22
CN1202887A (zh)	1998-12-23
NO981396L (no)	1998-05-27
EA000875B1 (ru)	2000-06-26
DE69622731T2 (de)	2003-02-20
AR005233A1 (es)	1999-04-28
HK1009133A1 (en)	1999-05-28
CN1130346C (zh)	2003-12-10
DE69622731D1 (de)	2002-09-05

Publication	Publication Date	Title
EP0854867B1 (en)	2002-07-31	Tetrahydroquinolines as nmda antagonists
EP0922034B1 (en)	2002-07-24	Tetrahydroquinoline derivatives as eaa antagonists
US5374648A (en)	1994-12-20	Indole derivatives and pharmaceutical use thereof
EP0813524A1 (en)	1997-12-29	Indole derivatives as eaa antagonists
AU731394B2 (en)	2001-03-29	Quinoline-2-carboxylic acid derivative and its use as excitatory amino acids antagonist
HK1009133B (en)	2003-02-28	Tetrahydroquinolines as nmda antagonists
MXPA99001557A (en)	1999-09-01	Tetrahydroquinoline derivatives as eaa antagonists