NO323781B1 - Nye fenylpiperaziner, fremgangsmate for fremstilling derav, farmasoytisk preparat inneholdende minst en slik forbindelse samt anvendelse av forbindelsene. - Google Patents

Nye fenylpiperaziner, fremgangsmate for fremstilling derav, farmasoytisk preparat inneholdende minst en slik forbindelse samt anvendelse av forbindelsene. Download PDF

Info

Publication number: NO323781B1
Authority: NO; Norway
Prior art keywords: compound; preparation; compounds; formula; processes
Prior art date: 2001-02-21

Application number

NO20025902A

Other languages

English (en)

Norwegian (no)

Other versions

NO20025902L (no

NO20025902D0 (no

Inventor

Gustaaf Johan Mar Scharrenburg

Roelof W Feenstra

Cornelis Gerrit Kruse

Eric Ronken

Andrew C Mccreary

Original Assignee

Solvay Pharm Bv

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.)

2001-02-21

Filing date

2002-12-09

Publication date

2007-07-02

2002-12-09 Application filed by Solvay Pharm Bv filed Critical Solvay Pharm Bv

2002-12-09 Publication of NO20025902L publication Critical patent/NO20025902L/no

2002-12-09 Publication of NO20025902D0 publication Critical patent/NO20025902D0/no

2007-07-02 Publication of NO323781B1 publication Critical patent/NO323781B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 32
238000002360 preparation method Methods 0.000 title claims description 9
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title claims description 5
238000000034 method Methods 0.000 title description 6
239000008194 pharmaceutical composition Substances 0.000 title 1
208000018737 Parkinson disease Diseases 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 2
208000015114 central nervous system disease Diseases 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
239000002274 desiccant Substances 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
229910004298 SiO 2 Inorganic materials 0.000 description 4
239000012267 brine Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
102000004980 Dopamine D2 Receptors Human genes 0.000 description 2
108090001111 Dopamine D2 Receptors Proteins 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000028017 Psychotic disease Diseases 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000000164 antipsychotic agent Substances 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
230000006399 behavior Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
-1 piperazine compound Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000000697 serotonin reuptake Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010003805 Autism Diseases 0.000 description 1
208000020706 Autistic disease Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
208000009132 Catalepsy Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
229940123603 Dopamine D2 receptor antagonist Drugs 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
208000012886 Vertigo Diseases 0.000 description 1
206010047853 Waxy flexibility Diseases 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000009194 climbing Effects 0.000 description 1
230000019771 cognition Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
239000003772 serotonin uptake inhibitor Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000028838 turning behavior Effects 0.000 description 1
231100000889 vertigo Toxicity 0.000 description 1

Classifications

- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D413/12—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 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
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/22—Anxiolytics
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems

Landscapes

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

NO20025902A 2001-02-21 2002-12-09 Nye fenylpiperaziner, fremgangsmate for fremstilling derav, farmasoytisk preparat inneholdende minst en slik forbindelse samt anvendelse av forbindelsene. NO323781B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01200609		2001-02-21
PCT/EP2002/001793 WO2002066472A1 (fr)	2001-02-21	2002-02-19	Derives de benzoxazolone presentant une affinite pour les recepteurs de reabsorption de dopamine et de serotonine

Publications (3)

Publication Number	Publication Date
NO20025902L NO20025902L (no)	2002-12-09
NO20025902D0 NO20025902D0 (no)	2002-12-09
NO323781B1 true NO323781B1 (no)	2007-07-02

Family

ID=8179908

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20025902A NO323781B1 (no)	2001-02-21	2002-12-09	Nye fenylpiperaziner, fremgangsmate for fremstilling derav, farmasoytisk preparat inneholdende minst en slik forbindelse samt anvendelse av forbindelsene.

Country Status (28)

Country	Link
US (1)	US6828325B2 (fr)
EP (1)	EP1395583B1 (fr)
JP (1)	JP4178033B2 (fr)
KR (1)	KR100848482B1 (fr)
CN (1)	CN1190433C (fr)
AR (1)	AR032711A1 (fr)
AT (1)	ATE289604T1 (fr)
AU (1)	AU2002253043B2 (fr)
BR (1)	BR0205220A (fr)
CA (1)	CA2411973A1 (fr)
CZ (1)	CZ299487B6 (fr)
DE (1)	DE60203042T2 (fr)
DK (1)	DK1395583T3 (fr)
DZ (1)	DZ3441A1 (fr)
ES (1)	ES2235029T3 (fr)
HU (1)	HUP0303329A3 (fr)
IL (1)	IL153176A (fr)
MX (1)	MXPA03004242A (fr)
NO (1)	NO323781B1 (fr)
NZ (1)	NZ523135A (fr)
PL (1)	PL359650A1 (fr)
PT (1)	PT1395583E (fr)
RU (1)	RU2279431C2 (fr)
SI (1)	SI1395583T1 (fr)
SK (1)	SK286064B6 (fr)
UA (1)	UA74426C2 (fr)
WO (1)	WO2002066472A1 (fr)
ZA (1)	ZA200209897B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ517900A (en)	1999-08-23	2003-08-29	Solvay Pharm Bv	Phenylpiperazines useful as serotonin reuptake inhibitors
AR032712A1 (es)	2001-02-21	2003-11-19	Solvay Pharm Bv	Un mesilato de derivados de fenilpiperazina y composiciones farmaceuticas que lo contienen
US7504395B2 (en) *	2001-07-20	2009-03-17	Psychogenics, Inc.	Treatment for attention-deficit hyperactivity disorder
EP1683790A1 (fr) *	2005-01-24	2006-07-26	Institut National De La Sante Et De La Recherche Medicale (Inserm)	Dérivés de 3,4-dihydro-2-naphtamide comme ligands selectifs de la dopamine D3
GB0708818D0 (en)	2007-05-08	2007-06-13	Portela & Ca Sa	Compounds
US8563567B2 (en)	2009-12-30	2013-10-22	Arqule, Inc.	Substituted heterocyclic compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0900792B1 (fr) *	1997-09-02	2003-10-29	Duphar International Research B.V	Dérivés de pipéridine et de pipérazine comme agonistes du récepteur 5-HT1
JP2003521443A (ja) *	1998-06-19	2003-07-15	ハー・ルンドベック・アクチエゼルスカベット	４，５，６及び７−インドール及びインドリン誘導体、その製造方法及びその使用方法
AR020773A1 (es) *	1998-10-16	2002-05-29	Duphar Int Res	Compuesto derivados de 3-(tetrahidropiridin-4-il)indol, metodo para prepararlo, una composicion farmaceutica que los contiene, metodo para preparar dicha composicion y uso del compuesto
NZ517900A (en)	1999-08-23	2003-08-29	Solvay Pharm Bv	Phenylpiperazines useful as serotonin reuptake inhibitors
EP1336406A1 (fr)	2002-02-14	2003-08-20	Solvay Pharmaceuticals B.V.	Agonistes partiels du récepteur D2 de la dopamine et inhibiteurs de la sérotonine et/ou de la noradrénaline

2002
- 2002-02-18 AR ARP020100547A patent/AR032711A1/es active IP Right Grant
- 2002-02-19 DZ DZ023441A patent/DZ3441A1/fr active
- 2002-02-19 HU HU0303329A patent/HUP0303329A3/hu unknown
- 2002-02-19 SI SI200230087T patent/SI1395583T1/xx unknown
- 2002-02-19 AT AT02722107T patent/ATE289604T1/de active
- 2002-02-19 BR BR0205220-2A patent/BR0205220A/pt not_active Application Discontinuation
- 2002-02-19 UA UA2003098663A patent/UA74426C2/uk unknown
- 2002-02-19 EP EP02722107A patent/EP1395583B1/fr not_active Expired - Lifetime
- 2002-02-19 KR KR1020027016845A patent/KR100848482B1/ko not_active Expired - Fee Related
- 2002-02-19 ES ES02722107T patent/ES2235029T3/es not_active Expired - Lifetime
- 2002-02-19 WO PCT/EP2002/001793 patent/WO2002066472A1/fr not_active Ceased
- 2002-02-19 CZ CZ20023933A patent/CZ299487B6/cs not_active IP Right Cessation
- 2002-02-19 NZ NZ523135A patent/NZ523135A/en unknown
- 2002-02-19 RU RU2003106194/04A patent/RU2279431C2/ru not_active IP Right Cessation
- 2002-02-19 MX MXPA03004242A patent/MXPA03004242A/es active IP Right Grant
- 2002-02-19 CN CNB02801684XA patent/CN1190433C/zh not_active Expired - Fee Related
- 2002-02-19 PL PL02359650A patent/PL359650A1/xx not_active IP Right Cessation
- 2002-02-19 IL IL153176A patent/IL153176A/en not_active IP Right Cessation
- 2002-02-19 US US10/343,232 patent/US6828325B2/en not_active Expired - Fee Related
- 2002-02-19 DE DE60203042T patent/DE60203042T2/de not_active Expired - Lifetime
- 2002-02-19 PT PT02722107T patent/PT1395583E/pt unknown
- 2002-02-19 SK SK1805-2002A patent/SK286064B6/sk not_active IP Right Cessation
- 2002-02-19 JP JP2002565986A patent/JP4178033B2/ja not_active Expired - Fee Related
- 2002-02-19 CA CA002411973A patent/CA2411973A1/fr not_active Abandoned
- 2002-02-19 DK DK02722107T patent/DK1395583T3/da active
- 2002-02-19 AU AU2002253043A patent/AU2002253043B2/en not_active Ceased
- 2002-12-05 ZA ZA200209897A patent/ZA200209897B/en unknown
- 2002-12-09 NO NO20025902A patent/NO323781B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP0303329A2 (hu)	2004-01-28
NO20025902L (no)	2002-12-09
NO20025902D0 (no)	2002-12-09
DZ3441A1 (fr)	2002-08-29
EP1395583A1 (fr)	2004-03-10
JP2004518746A (ja)	2004-06-24
ATE289604T1 (de)	2005-03-15
MXPA03004242A (es)	2003-09-22
SK18052002A3 (sk)	2003-05-02
CA2411973A1 (fr)	2002-08-29
BR0205220A (pt)	2003-06-24
NZ523135A (en)	2005-02-25
JP4178033B2 (ja)	2008-11-12
DK1395583T3 (da)	2005-03-29
SI1395583T1 (fr)	2005-08-31
RU2279431C2 (ru)	2006-07-10
AR032711A1 (es)	2003-11-19
SK286064B6 (sk)	2008-02-05
ES2235029T3 (es)	2005-07-01
CZ20023933A3 (cs)	2003-03-12
EP1395583B1 (fr)	2005-02-23
PT1395583E (pt)	2005-06-30
DE60203042T2 (de)	2006-01-19
IL153176A (en)	2012-10-31
WO2002066472A1 (fr)	2002-08-29
US20030162791A1 (en)	2003-08-28
UA74426C2 (uk)	2005-12-15
AU2002253043B2 (en)	2006-06-08
PL359650A1 (en)	2004-08-23
CN1190433C (zh)	2005-02-23
US6828325B2 (en)	2004-12-07
DE60203042D1 (de)	2005-03-31
KR100848482B1 (ko)	2008-07-28
ZA200209897B (en)	2004-03-05
KR20030072215A (ko)	2003-09-13
HK1059781A1 (en)	2004-07-16
CN1463269A (zh)	2003-12-24
IL153176A0 (en)	2003-06-24
CZ299487B6 (cs)	2008-08-13
HUP0303329A3 (en)	2008-12-29

Legal Events

Date	Code	Title	Description
2012-10-01	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP1212320B1 (fr)	2005-07-06	Phenylpiperazines comme inhibiteurs de recapture de serotonine
NO320970B1 (no)	2006-02-20	Piperazin- og piperidinforbindelse, fremgangsmate for fremstilling derav, farmasoytiske sammensetninger som innbefatter slike forbindelser, fremgangsmate for fremstilling av de nevnte farmasoytiske sammensetninger, samt anvendelse av disse for behandling av CNS-forstyrrelser
EP0908458B1 (fr)	2006-01-25	Dérivés der pyridylmethylpiperazine et piperidine substitués, leur préparation et leur utilisation pour le traitment de désordres du système nerveux central (SNC)
NO318888B1 (no)	2005-05-18	Nye piperazin- og piperidinforbindelser, fremgangsmater for fremstilling derav, farmasoytiske preparater og fremgangsmater for fremstilling av disse samt anvendelse av forbindelsene.
AU2002253043B2 (en)	2006-06-08	New phenylpiperazines
CZ20011353A3 (cs)	2001-09-12	(3-tetrahydropyridin-4-yl)indoly pro léčbu psychotických poruch
AU2002253043A1 (en)	2003-02-27	New phenylpiperazines
AU2002253043A2 (en)	2003-06-19	New phenylpiperazines
HK1059781B (en)	2005-05-13	New phenylpiperazines
HK1018272B (en)	2006-04-13	Substituted pyridylmethylpiperazine and piperidine derivatives, their preparation and their use for treating central nervous system (cns) disorders