ZA200401724B - Salts of substituted 1,2,3,4-tetrahydroquinoline-2-carboxylic acid derivatives as NMDA antagonists. - Google Patents

Salts of substituted 1,2,3,4-tetrahydroquinoline-2-carboxylic acid derivatives as NMDA antagonists. Download PDF

Info

Publication number: ZA200401724B
Authority: ZA; South Africa
Prior art keywords: unsubstituted; polysubstituted; monosubstituted; alkyl; unbranched
Prior art date: 2001-08-03

Application number

ZA200401724A

Other languages

English (en)

Inventor

Corinna Sundermann

Werner Guenter Englberger

Michael Przewosny

Original Assignee

Gruenenthal Gmbh

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.)

2001-08-03

Filing date

2004-03-02

Publication date

2005-02-01

2004-03-02 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

2005-02-01 Publication of ZA200401724B publication Critical patent/ZA200401724B/en

Links

150000003839 salts Chemical class 0.000 title claims description 61
OSJVTYVKQNOXPP-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)CCC2=C1 OSJVTYVKQNOXPP-UHFFFAOYSA-N 0.000 title claims description 12
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 description 7
239000005557 antagonist Substances 0.000 title description 6
125000003118 aryl group Chemical group 0.000 claims description 52
-1 l-adamantyl Chemical group 0.000 claims description 52
229920006395 saturated elastomer Polymers 0.000 claims description 34
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000004432 carbon atom Chemical group C* 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 28
125000000623 heterocyclic group Chemical group 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 23
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 22
239000000126 substance Substances 0.000 claims description 21
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208000002193 Pain Diseases 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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150000001768 cations Chemical class 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
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125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
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DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
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125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229940116229 borneol Drugs 0.000 claims description 2
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159000000007 calcium salts Chemical class 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 2
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125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
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239000007795 chemical reaction product Substances 0.000 claims 3
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 3
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
208000009205 Tinnitus Diseases 0.000 claims 2
208000000323 Tourette Syndrome Diseases 0.000 claims 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
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VQMSRUREDGBWKT-UHFFFAOYSA-N cinchoninic acid Natural products C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 claims 2
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 2
231100000886 tinnitus Toxicity 0.000 claims 2
JDIMOBLZDWICDJ-UHFFFAOYSA-N 1,3-dichloro-5,6,6a,7,8,12b-hexahydrobenzo[k]phenanthridine-6-carboxylic acid Chemical compound C1=CC=C2C3C4=C(Cl)C=C(Cl)C=C4NC(C(=O)O)C3CCC2=C1 JDIMOBLZDWICDJ-UHFFFAOYSA-N 0.000 claims 1
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Classifications

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- 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
- A61P25/32—Alcohol-abuse
- 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
- A61P25/36—Opioid-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Addiction (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Rheumatology (AREA)
Ophthalmology & Optometry (AREA)
Endocrinology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Psychology (AREA)
Virology (AREA)
AIDS & HIV (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Hospice & Palliative Care (AREA)
Tropical Medicine & Parasitology (AREA)
Emergency Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)

ZA200401724A 2001-08-03 2004-03-02 Salts of substituted 1,2,3,4-tetrahydroquinoline-2-carboxylic acid derivatives as NMDA antagonists. ZA200401724B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10137488A DE10137488A1 (de)	2001-08-03	2001-08-03	Salze substituierter 1,2,3,4-Tetrahydrochinolin-2-carbonsäurederivate

Publications (1)

Publication Number	Publication Date
ZA200401724B true ZA200401724B (en)	2005-02-01

Family

ID=7693858

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200401724A ZA200401724B (en)	2001-08-03	2004-03-02	Salts of substituted 1,2,3,4-tetrahydroquinoline-2-carboxylic acid derivatives as NMDA antagonists.

Country Status (18)

Country	Link
US (1)	US20040224969A1 (fr)
EP (1)	EP1411947A2 (fr)
JP (1)	JP2005501839A (fr)
KR (1)	KR20040043177A (fr)
CN (1)	CN1561215A (fr)
BR (1)	BR0211733A (fr)
CA (1)	CA2456103A1 (fr)
CO (1)	CO5550424A2 (fr)
DE (1)	DE10137488A1 (fr)
EC (1)	ECSP044969A (fr)
HU (1)	HUP0401251A2 (fr)
IL (1)	IL160162A0 (fr)
MX (1)	MXPA04000952A (fr)
NO (1)	NO20040423L (fr)
PL (1)	PL369502A1 (fr)
RU (1)	RU2004106531A (fr)
WO (1)	WO2003013530A2 (fr)
ZA (1)	ZA200401724B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0301320D0 (sv) *	2003-05-06	2003-05-06	Astrazeneca Ab	Positive modulators of nicotinic acetylcholine receptors
US20090203726A1 (en) *	2007-11-30	2009-08-13	Maxthera Inc.	Substituted tetrahydroquinolines as antibacterial agents
IL295569B1 (en) *	2020-03-19	2026-04-01	Arcus Biosciences Inc	Tetralin and tetrahydroquinoline compounds as inhibitors of HIF-2ALPHA

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5017584A (en) *	1984-12-20	1991-05-21	Sterling Drug Inc.	Antidepressant 2-(4,5-dihydro-1H-imidazolyl)-dihydro-1H-indoles, -1,2,3,4-tetrahydroquinolines and -1H-indoles, and methods of use thereas
US4906621A (en) *	1985-05-24	1990-03-06	Ciba-Geigy Corporation	Certain 2-carboxypiperidyl-alkylene phosphonic acids and esters thereof useful for the treatment of disorders responsive to N-methyl-D-aspartate receptor blockade
ATE147732T1 (de) *	1989-03-08	1997-02-15	Merck Sharp & Dohme	Tetrahydroquinolin-derivate, verwendbar bei neurodegenerativen krankheiten
US5925527A (en) *	1997-02-04	1999-07-20	Trega Biosciences, Inc.	Tricyclic Tetrahydroquinoline derivatives and tricyclic tetrahydroquinoline combinatorial libraries
WO1998034115A1 (fr) *	1997-02-04	1998-08-06	Trega Biosciences, Inc.	Derives de la quinoline substituee en 4- et bibliotheques combinatoires les contenant
MY125037A (en) *	1998-06-10	2006-07-31	Glaxo Wellcome Spa	1,2,3,4 tetrahydroquinoline derivatives
DE10005302A1 (de) *	2000-02-07	2002-01-17	Gruenenthal Gmbh	Substituierte 1,2,3,4-Tetrahydrochinolin-2-carbonsäurederivate

2001
- 2001-08-03 DE DE10137488A patent/DE10137488A1/de not_active Withdrawn
2002
- 2002-08-05 PL PL02369502A patent/PL369502A1/xx not_active Application Discontinuation
- 2002-08-05 JP JP2003518539A patent/JP2005501839A/ja not_active Withdrawn
- 2002-08-05 CA CA002456103A patent/CA2456103A1/fr not_active Abandoned
- 2002-08-05 IL IL16016202A patent/IL160162A0/xx unknown
- 2002-08-05 CN CNA028194136A patent/CN1561215A/zh active Pending
- 2002-08-05 KR KR10-2004-7001633A patent/KR20040043177A/ko not_active Withdrawn
- 2002-08-05 EP EP02772122A patent/EP1411947A2/fr not_active Withdrawn
- 2002-08-05 WO PCT/EP2002/008729 patent/WO2003013530A2/fr not_active Ceased
- 2002-08-05 HU HU0401251A patent/HUP0401251A2/hu unknown
- 2002-08-05 MX MXPA04000952A patent/MXPA04000952A/es unknown
- 2002-08-05 RU RU2004106531/04A patent/RU2004106531A/ru not_active Application Discontinuation
- 2002-08-05 BR BR0211733-9A patent/BR0211733A/pt not_active IP Right Cessation
2004
- 2004-01-30 NO NO20040423A patent/NO20040423L/no not_active Application Discontinuation
- 2004-02-02 EC EC2004004969A patent/ECSP044969A/es unknown
- 2004-02-03 CO CO04008311A patent/CO5550424A2/es not_active Application Discontinuation
- 2004-02-03 US US10/770,123 patent/US20040224969A1/en not_active Abandoned
- 2004-03-02 ZA ZA200401724A patent/ZA200401724B/en unknown

Also Published As

Publication number	Publication date
PL369502A1 (en)	2005-04-18
CA2456103A1 (fr)	2003-02-20
JP2005501839A (ja)	2005-01-20
BR0211733A (pt)	2004-09-21
EP1411947A2 (fr)	2004-04-28
HUP0401251A2 (hu)	2004-10-28
RU2004106531A (ru)	2005-07-27
US20040224969A1 (en)	2004-11-11
MXPA04000952A (es)	2004-04-20
ECSP044969A (es)	2004-03-23
WO2003013530A3 (fr)	2003-09-25
WO2003013530A2 (fr)	2003-02-20
DE10137488A1 (de)	2003-02-20
KR20040043177A (ko)	2004-05-22
IL160162A0 (en)	2004-07-25
CO5550424A2 (es)	2005-08-31
NO20040423L (no)	2004-03-08
CN1561215A (zh)	2005-01-05

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AU2002321215B2 (en)	2007-08-02	Substituted 4-aminocyclohexanols
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AU2002328894B2 (en)	2007-06-14	Substituted 4-aminocyclohexanol derivatives
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HK1075205B (en)	2009-04-24	Combination of selected opioids with muscarine antagonists for treating urinary incontinence
WO2003068734A1 (fr)	2003-08-21	Esters de carbamide pour traiter la douleur
DE10135635A1 (de)	2003-02-06	Analgetische substituierte 4-Aminocyclohexanolderivate