WO1998014444A1 - Derives de n-(benzothiazol-2-yl)piperidine-1-ethanamine, leur preparation et leur application en therapeutique - Google Patents

Derives de n-(benzothiazol-2-yl)piperidine-1-ethanamine, leur preparation et leur application en therapeutique Download PDF

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Publication number
WO1998014444A1
WO1998014444A1 PCT/FR1997/001692 FR9701692W WO9814444A1 WO 1998014444 A1 WO1998014444 A1 WO 1998014444A1 FR 9701692 W FR9701692 W FR 9701692W WO 9814444 A1 WO9814444 A1 WO 9814444A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
compound
mixture
reacted
piperidine
Prior art date
Application number
PCT/FR1997/001692
Other languages
English (en)
French (fr)
Inventor
Gihad Dargazanli
Pascal George
Patrick Lardenois
Jonathan Frost
Johannes Schoemaker
Maria-Carmen Renones
Pascale Magat
Original Assignee
Synthelabo
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.)
Filing date
Publication date
Priority to CA002266510A priority Critical patent/CA2266510A1/en
Priority to JP10516272A priority patent/JP2001501217A/ja
Priority to IL12890297A priority patent/IL128902A/en
Priority to PL97332648A priority patent/PL332648A1/xx
Priority to EP97943001A priority patent/EP0929550A1/fr
Priority to SK422-99A priority patent/SK42299A3/sk
Priority to NZ334553A priority patent/NZ334553A/xx
Priority to EEP199900135A priority patent/EE9900135A/xx
Priority to BR9711842A priority patent/BR9711842A/pt
Priority to AU44638/97A priority patent/AU722147B2/en
Application filed by Synthelabo filed Critical Synthelabo
Publication of WO1998014444A1 publication Critical patent/WO1998014444A1/fr
Priority to BG103271A priority patent/BG103271A/xx
Priority to NO991581A priority patent/NO991581L/no

Links

Classifications

    • 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
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • 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

Definitions

  • n represents the number 0, 1, 2 or 3
  • R represents a hydrogen or halogen atom or a methyl or methoxy group
  • R 2 represents a hydrogen atom or a methyl group
  • R 3 represents a hydrogen atom or one or two halogen atoms.
  • the compounds of the invention may exist in the form of free bases or of addition salts with acids.
  • amide at a temperature of 50 to 80 ° C. , and in the presence of a mineral base, for example potassium carbonate.
  • a simple or complex reducing agent such as an alkali metal hydride, for example, lithium aluminum hydride, boron hydride, boron hydride-tetrahydro
  • a piperidine of general formula (V), in which n and R 3 are as defined above, is reacted with l-bromo-2-chloroethane, under the conventional conditions for such a reaction, it that is to say in a polar solvent, for example N, iV-dimethylformamide, in the presence of a mineral base, for example potassium carbonate, at a temperature of 50 to 80 ° C.
  • a polar solvent for example N, iV-dimethylformamide
  • a mineral base for example potassium carbonate
  • N- (Benzothiazolyl-2-yl) -4- [(4-fluorophenyl) methyl] piperidine-1 -ethanamine, ethanedioate 1.3 g (0.00349 mole) of N- (benzothiazolyl-) are introduced into a 250 ml three-necked flask 2-yl) -4- [(4-fluorophenyl) methyl] piperidme-1-acetamide in solution in 25 ml of dry tetrahydrofuran, 1.09 ml, or 3 equivalents, of borane-methyl sulfide complex is added, and heats the mixture at reflux for 4 hours.
  • a suspension of 0.854 g (0.0224 mole) of lithium aluminum hydride in 50 ml of tetrahydrofuran is prepared, it is heated to reflux, a solution of 2 g (0.0112 mole) of intermediate is added. formylated in 100 ml of tetrahydrofuran and heating is continued for 30 mm. The mixture is cooled, 100 ml of ethyl acetate are added and, dropwise, 38 ml of water, the organic phase is separated by decantation, it is evaporated under reduced pressure, the crystallized residue is triturated in petroleum ether, it is filtered and dried in the presence of phosphorus pentoxide. 1.5 g of compound are obtained.
  • N- (Benzothiazol-2 -yl) -4- [2- (4-fluorophenyl) ethyl] piperidine-1-ethanamine 0.96 g (0.025 mole) of lithium aluminum hydride and 140 ml of dry tetrahydrofuran are introduced into a 500 ml three-necked flask, under nitrogen atmosphere, the suspension is heated to reflux, drip, 5.0 g (0.01 mole) of N- (benzothiazol -2 -yl) -4- [2- (4-fluorophenyl) - ethyl] piperidine-1-acetamide dissolved in 60 ml of tetrahydrofuran dry and heating continues 30 min.
  • the compounds of the invention have been subjected to tests which have demonstrated their interest as therapeutic active substances.
  • test compounds are administered after intravenous occlusion. 24 hours after occlusion of the middle cerebral artery, the animals are sacrificed and the brain is removed.
  • the volume of the cerebral infarction is evaluated from the measurement of the surface of the necrosis on 6 coronal sections stained with 2, 3, 5-t ⁇ phenyltetrazol ⁇ um chloride.
  • compound No. ll of the above table significantly reduces the volume of the infarction by approximately
  • the compounds of the invention were also subjected to the test of global cerebral ischemia in mice.
  • the ischemia is due to cardiac arrest induced by a rapid intravenous injection of magnesium chloride.
  • the "survival time” is measured, that is to say the interval between the moment of injection of magnesium chloride and the last observable respiratory movement of each mouse. This last movement is considered the ultimate index of a function of the central nervous system. Respiratory arrest occurs approximately 19 seconds after the injection of magnesium chloride.
  • Male mice (Charles River CD1) are studied in groups of 10. They are fed and watered ad libitum before the tests. The survival time is measured 10 minutes after the intraperitoneal administration of the compounds of the invention.
  • the results are given in the form of the difference between the survival time measured in a group of 10 mice having received the compound and the survival time measured in a group of 10 mice having received the carrier liquid.
  • the relationships between the modifications in the survival term and the dose of the compound are recorded graphically according to a semilogarithmic curve.
  • a 3 second increase in survival time is both statistically significant and reproducible.
  • the ED 3 ride of the most active compounds of the invention are less than 5 mg / kg intraperitoneally.
  • the compounds according to the invention have also been the subject of an in vitro study as to their affinity for the dopaminergic receptors D 4 obtained by transfection of human receptors D 4 ⁇ 4 into CHO cells, essentially as described by Van Toi . et al., Nature (1991) 350 610-614 and Van Toi. et al., Nature (1992) 358 149-152.
  • the membrane suspension (100 ⁇ l, 78 ⁇ g of membrane) is incubated at 25 ° C for 60 min in the presence of 0.5 nM of [ 3 H] spiperone (specific activity 17 to 20 Ci / mmol, New England Nuclear / Du Pont de Nemours, Boston, MA, USA) in a final volume of 1 ml of incubation buffer in the presence or absence of the test compound.
  • the filters are dried in an oven at 120 ° C for 5 min.
  • the radioactivity retained on the filters is determined by liquid scintigraphy.
  • the non-specific binding is determined in the presence of 1 ⁇ M of haloperidol.
  • the percentage inhibition of the specific binding of [ 3 H] spiperone is calculated, then the IC 50 , concentration which inhibits 50% of the binding, is determined.
  • the IC 50 values of the compounds of the invention are of the order of 3 to 30 nM.
  • results of the tests show that, in vivo, the compounds according to the invention have neuroprotective properties and that, in vi tro, they displace the specific binding of [ 3 H] spiperone to human D 4 4 dopaminergic receptors.
  • ischemic or hypoxic origin Cerebral infarction, cranial or spinal trauma, cardiac or respiratory arrest, transient ischemic attack, perinatal asphyxia
  • glaucoma progressive neurodegenerative diseases
  • senile dementia such as Alzheimer's disease, vascular dementias, Parkinson's disease, Huntington's disease, olivo-ponto-cerebellar atrophy, amyotrophic lateral sclerosis, neurodegenerative diseases of viral origin, etc.
  • senile dementia such as Alzheimer's disease, vascular dementias, Parkinson's disease, Huntington's disease, olivo-ponto-cerebellar atrophy, amyotrophic lateral sclerosis, neurodegenerative diseases of viral origin, etc.
  • psychoses in particular schizophrenia (deficit and productive forms) and acute and chronic extrapyramidal symptoms, induced by neuroleptics or consecutive to Parkinson's disease, for the treatment various forms of anxiety, panic attacks, phobias, obsessive compulsive disorder, for the treatment of various forms of depression, including psychotic depression, for the treatment of drug and alcohol dependence and disorders of the hypothalamic-pituitary function, and for the treatment cognitive impairment related to age or Alzheimer's disease.
  • psychoses in particular schizophrenia (deficit and productive forms) and acute and chronic extrapyramidal symptoms, induced by neuroleptics or consecutive to Parkinson's disease
  • various forms of anxiety, panic attacks, phobias, obsessive compulsive disorder for the treatment of various forms of depression, including psychotic depression, for the treatment of drug and alcohol dependence and disorders of the hypothalamic-pituitary function, and for the treatment cognitive impairment related to age or Alzheimer's disease.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
PCT/FR1997/001692 1996-10-01 1997-09-26 Derives de n-(benzothiazol-2-yl)piperidine-1-ethanamine, leur preparation et leur application en therapeutique WO1998014444A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
BR9711842A BR9711842A (pt) 1996-10-01 1997-09-26 Derivados de n-(benzotiazol-2-il) piperidina-1-etanamina sua prepara-Æo e sua aplica-Æo em terap-utica
IL12890297A IL128902A (en) 1996-10-01 1997-09-26 History - N- (2-Benzothiazol) - 1 piperidinethanamine, their preparation and pharmaceutical preparations containing them
PL97332648A PL332648A1 (en) 1996-10-01 1997-09-26 Derivatives of n-(2-benzothiazolyl)-1-piperidinethane mine, their production and application in medical therapy
EP97943001A EP0929550A1 (fr) 1996-10-01 1997-09-26 DERIVES DE $i(N)-(BENZOTHIAZOL-2-YL)PIPERIDINE-1-ETHANAMINE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
SK422-99A SK42299A3 (en) 1996-10-01 1997-09-26 N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics
CA002266510A CA2266510A1 (en) 1996-10-01 1997-09-26 N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics
EEP199900135A EE9900135A (et) 1996-10-01 1997-09-26 N-(2-bensotiasolüül)-1-piperidiinetaanamiini derivaadid, nende valmistamine ja kasutamine raviks
NZ334553A NZ334553A (en) 1996-10-01 1997-09-26 N-(2-Benzothiazolyl) piperidine-1 ethanamine derivatives and pharmaceutical use
AU44638/97A AU722147B2 (en) 1996-10-01 1997-09-26 N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics
JP10516272A JP2001501217A (ja) 1996-10-01 1997-09-26 Ｎ―（ベンゾチアゾール―２―イル）―１―ピペリジンエタナミン誘導体、その製法および治療的応用
BG103271A BG103271A (en) 1996-10-01 1999-03-22 Derivatives of n-(benzothiazol-2-yl) piperidine-1-ethaneamines, method for their preparation and application as therapeutical means
NO991581A NO991581L (no) 1996-10-01 1999-03-30 N-(benzotiazol-2-yl)piperidin-1-etanaminderivater, deres fremstilling og anvendelse i terapeutiske midler

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR96/11925 1996-10-01
FR9611925A FR2753970B1 (fr) 1996-10-01 1996-10-01 Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique

Publications (1)

Publication Number Publication Date
WO1998014444A1 true WO1998014444A1 (fr) 1998-04-09

Family

ID=9496217

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR1997/001692 WO1998014444A1 (fr) 1996-10-01 1997-09-26 Derives de n-(benzothiazol-2-yl)piperidine-1-ethanamine, leur preparation et leur application en therapeutique

Country Status (23)

Country Link
EP (1) EP0929550A1 (cs)
JP (1) JP2001501217A (cs)
KR (1) KR20000048767A (cs)
CN (1) CN1230959A (cs)
AR (1) AR009105A1 (cs)
AU (1) AU722147B2 (cs)
BG (1) BG103271A (cs)
BR (1) BR9711842A (cs)
CA (1) CA2266510A1 (cs)
CO (1) CO4650030A1 (cs)
CZ (1) CZ112699A3 (cs)
EE (1) EE9900135A (cs)
FR (1) FR2753970B1 (cs)
HU (1) HUP9904091A3 (cs)
IL (1) IL128902A (cs)
NO (1) NO991581L (cs)
NZ (1) NZ334553A (cs)
PL (1) PL332648A1 (cs)
SK (1) SK42299A3 (cs)
TR (1) TR199900634T2 (cs)
TW (1) TW438800B (cs)
WO (1) WO1998014444A1 (cs)
ZA (1) ZA978772B (cs)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6407122B1 (en) * 1997-12-02 2002-06-18 Pharmacia & Upjohn S.P.A. Amino-benzothiazole derivatives
US7317007B2 (en) 2000-06-21 2008-01-08 Hoffmann-La Roche Inc. Benzothiazole derivatives with activity as adenosine receptor ligands

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6107313A (en) * 1998-10-02 2000-08-22 Combichem, Inc. Dopamine receptor antagonists
US7087761B2 (en) 2003-01-07 2006-08-08 Hoffmann-La Roche Inc. Cyclization process for substituted benzothiazole derivatives
EP1680408A2 (en) * 2003-10-24 2006-07-19 F. Hoffmann-La Roche Ag Ccr3 receptor antagonists
PL1753760T3 (pl) 2004-05-24 2008-06-30 Hoffmann La Roche (4-metoksy-7-morffolin-4-ylobenzatiazol-2-ilo)amid kwasu 4-hydroksy-4-metylopiperydyno-1-karboksylowego
US7459563B2 (en) 2004-11-05 2008-12-02 Hoffmann-La Roche Inc. Process for the preparation of isonicotinic acid derivatives
MX2007011483A (es) 2005-03-23 2007-10-12 Hoffmann La Roche Derivados de acetilenil-pirazolo-pirimidina como antagonistas de glutamato metabotropico 2.
KR101121292B1 (ko) 2005-09-27 2012-04-13 에프. 호프만-라 로슈 아게 Ｍｇｌｕｒ2 길항제로서 옥사다이아졸일 피라졸로-피리미딘

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0184257A1 (en) * 1984-12-03 1986-06-11 Janssen Pharmaceutica N.V. Benzoxazol- and benzothiazolamine derivatives
EP0199400A2 (en) * 1985-04-15 1986-10-29 Janssen Pharmaceutica N.V. Substituted N-[(4-piperidinyl)alkyl] bicyclic condensed ozazol- and thiazolamines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0184257A1 (en) * 1984-12-03 1986-06-11 Janssen Pharmaceutica N.V. Benzoxazol- and benzothiazolamine derivatives
EP0199400A2 (en) * 1985-04-15 1986-10-29 Janssen Pharmaceutica N.V. Substituted N-[(4-piperidinyl)alkyl] bicyclic condensed ozazol- and thiazolamines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
G.FOSCOLOS ET AL: "Synthèse et étude pharmacodynamique de nouveaux dérivés du benzothiazole", ANNALES PHARMACEUTIQUES FRANCAISES, vol. 35, no. 7, July 1977 (1977-07-01), PARIS FR, pages 295 - 307, XP002032293 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6407122B1 (en) * 1997-12-02 2002-06-18 Pharmacia & Upjohn S.P.A. Amino-benzothiazole derivatives
US7317007B2 (en) 2000-06-21 2008-01-08 Hoffmann-La Roche Inc. Benzothiazole derivatives with activity as adenosine receptor ligands

Also Published As

Publication number Publication date
PL332648A1 (en) 1999-09-27
AU722147B2 (en) 2000-07-20
HUP9904091A3 (en) 2000-07-28
BR9711842A (pt) 1999-08-24
CO4650030A1 (es) 1998-09-03
NO991581D0 (no) 1999-03-30
NO991581L (no) 1999-06-01
JP2001501217A (ja) 2001-01-30
TW438800B (en) 2001-06-07
SK42299A3 (en) 1999-12-10
FR2753970B1 (fr) 1998-10-30
KR20000048767A (ko) 2000-07-25
CN1230959A (zh) 1999-10-06
NZ334553A (en) 2000-11-24
IL128902A (en) 2001-07-24
CZ112699A3 (cs) 1999-06-16
IL128902A0 (en) 2000-02-17
EE9900135A (et) 1999-12-15
AU4463897A (en) 1998-04-24
BG103271A (en) 2000-05-31
ZA978772B (en) 1998-03-27
FR2753970A1 (fr) 1998-04-03
CA2266510A1 (en) 1998-04-09
EP0929550A1 (fr) 1999-07-21
AR009105A1 (es) 2000-03-08
TR199900634T2 (xx) 1999-06-21
HUP9904091A2 (hu) 2000-05-28

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