ZA200103251B - 3-Tetrahydropyridin-4-YL indoles for treatment of psychotic disorders. - Google Patents

3-Tetrahydropyridin-4-YL indoles for treatment of psychotic disorders. Download PDF

Info

Publication number: ZA200103251B
Authority: ZA; South Africa
Prior art keywords: compound; composition; formula; new; substance
Prior art date: 1998-10-16

Application number

ZA200103251A

Other languages

English (en)

Inventor

Marthius T M Tulp

Bernard Van Vliet

Roelof Van Hes

Gerben Visser

Johannes A M Van Der Heiden

Jacobus Tipker

Cornelis G Kruse

Original Assignee

Duphar Int Res

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.)

1998-10-16

Filing date

2001-04-20

Publication date

2002-07-22

2001-04-20 Application filed by Duphar Int Res filed Critical Duphar Int Res

2002-07-22 Publication of ZA200103251B publication Critical patent/ZA200103251B/en

Links

208000028017 Psychotic disease Diseases 0.000 title description 2
UVHQBWHIEIBOSH-UHFFFAOYSA-N 3-(1,2,3,4-tetrahydropyridin-4-yl)-1h-indole Chemical class C1=CNCCC1C1=CNC2=CC=CC=C12 UVHQBWHIEIBOSH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 40
238000000034 method Methods 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 4
-1 amine compound Chemical class 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
208000015114 central nervous system disease Diseases 0.000 claims 2
239000003814 drug Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000002585 base Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
229960003638 dopamine Drugs 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
NOBJPJHWOFGLFA-UHFFFAOYSA-N 5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1C1=CCNCC1 NOBJPJHWOFGLFA-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
125000004093 cyano group Chemical group *C#N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
150000002475 indoles Chemical class 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
230000000697 serotonin reuptake Effects 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000020114 Schizophrenia and other psychotic disease Diseases 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
230000000949 anxiolytic effect Effects 0.000 description 2
229940005530 anxiolytics Drugs 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
229940125904 compound 1 Drugs 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000003772 serotonin uptake inhibitor Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 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
IYVSWFIJIOPUDN-UHFFFAOYSA-N 1-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)indole Chemical compound C12=CC=CC=C2N(C)C=C1C1=CCNCC1 IYVSWFIJIOPUDN-UHFFFAOYSA-N 0.000 description 1
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 1
QISSVLCQDNIJCS-UHFFFAOYSA-N 2-fluoro-1h-indole Chemical compound C1=CC=C2NC(F)=CC2=C1 QISSVLCQDNIJCS-UHFFFAOYSA-N 0.000 description 1
CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
XVMKZAAFVWXIII-UHFFFAOYSA-N 5-fluoro-2-benzofuran-1,3-dione Chemical compound FC1=CC=C2C(=O)OC(=O)C2=C1 XVMKZAAFVWXIII-UHFFFAOYSA-N 0.000 description 1
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
208000019901 Anxiety disease Diseases 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
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 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940054051 antipsychotic indole derivative Drugs 0.000 description 1
229940005529 antipsychotics 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
238000010533 azeotropic distillation Methods 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
230000001143 conditioned effect Effects 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 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
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
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000889 vertigo Toxicity 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
- C07D401/14—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 three or more hetero rings
- 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
- 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
- A61P25/22—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

Landscapes

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

ZA200103251A 1998-10-16 2001-04-20 3-Tetrahydropyridin-4-YL indoles for treatment of psychotic disorders. ZA200103251B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98203499		1998-10-16

Publications (1)

Publication Number	Publication Date
ZA200103251B true ZA200103251B (en)	2002-07-22

Family

ID=8234230

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200103251A ZA200103251B (en)	1998-10-16	2001-04-20	3-Tetrahydropyridin-4-YL indoles for treatment of psychotic disorders.

Country Status (28)

Country	Link
US (1)	US6391896B1 (fr)
EP (1)	EP1121356B1 (fr)
JP (1)	JP4659984B2 (fr)
KR (1)	KR100619464B1 (fr)
CN (1)	CN1140524C (fr)
AR (1)	AR020773A1 (fr)
AT (1)	ATE230741T1 (fr)
AU (1)	AU750811B2 (fr)
BR (1)	BR9914582A (fr)
CA (1)	CA2346896C (fr)
CZ (1)	CZ20011353A3 (fr)
DE (1)	DE69904849T2 (fr)
DK (1)	DK1121356T3 (fr)
DZ (1)	DZ2917A1 (fr)
ES (1)	ES2188260T3 (fr)
HU (1)	HUP0104701A3 (fr)
IL (2)	IL142589A0 (fr)
NO (1)	NO320531B1 (fr)
NZ (1)	NZ511289A (fr)
PL (1)	PL195734B1 (fr)
RU (1)	RU2222535C2 (fr)
SI (1)	SI1121356T1 (fr)
SK (1)	SK285764B6 (fr)
TR (1)	TR200101808T2 (fr)
TW (1)	TW577884B (fr)
UA (1)	UA66888C2 (fr)
WO (1)	WO2000023441A1 (fr)
ZA (1)	ZA200103251B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002544223A (ja) *	1999-05-12	2002-12-24	ソルベイ・フアーマシユーチカルズ・ベー・ブイ	精神病性障害の治療方法
WO2001014330A2 (fr)	1999-08-23	2001-03-01	Solvay Pharmaceuticals B.V.	Nouvelles phenylpiperazines
AR032712A1 (es) *	2001-02-21	2003-11-19	Solvay Pharm Bv	Un mesilato de derivados de fenilpiperazina y composiciones farmaceuticas que lo contienen
AR032711A1 (es) *	2001-02-21	2003-11-19	Solvay Pharm Bv	Derivados de fenilpiperazina, un metodo para la preparacion de los mismos y una composicion farmaceutica que los contiene
US7371769B2 (en)	2004-12-07	2008-05-13	Solvay Pharmaceuticals B.V.	Tetrahydropyridin-4-yl indoles with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites
US8101619B2 (en)	2004-12-08	2012-01-24	Solvay Pharmaceuticals B.V.	Phenylpiperazine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition
EP1890869B1 (fr)	2005-04-06	2008-10-15	3M Innovative Properties Company	Corps optiques contenant des couches limites pelables rugueuses et des structures asymetriques en surface
US9709700B2 (en) *	2005-04-06	2017-07-18	3M Innovative Properties Company	Optical bodies including rough strippable boundary layers
US20060227421A1 (en) *	2005-04-06	2006-10-12	Stover Carl A	Optical bodies including strippable boundary layers

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4414113A1 (de) *	1994-04-22	1995-10-26	Merck Patent Gmbh	3-Indolylpiperidine
US5576321A (en)	1995-01-17	1996-11-19	Eli Lilly And Company	Compounds having effects on serotonin-related systems
ZA9711376B (en)	1996-12-20	1998-07-21	Lundbeck & Co As H	Indole or dihydroindole derivatives

1999
- 1999-10-12 AR ARP990105138A patent/AR020773A1/es active IP Right Grant
- 1999-10-13 TW TW088117668A patent/TW577884B/zh not_active IP Right Cessation
- 1999-10-15 HU HU0104701A patent/HUP0104701A3/hu unknown
- 1999-10-15 US US09/807,408 patent/US6391896B1/en not_active Expired - Lifetime
- 1999-10-15 IL IL14258999A patent/IL142589A0/xx active IP Right Grant
- 1999-10-15 CN CNB998135801A patent/CN1140524C/zh not_active Expired - Fee Related
- 1999-10-15 CA CA002346896A patent/CA2346896C/fr not_active Expired - Fee Related
- 1999-10-15 AU AU64741/99A patent/AU750811B2/en not_active Ceased
- 1999-10-15 WO PCT/EP1999/007912 patent/WO2000023441A1/fr not_active Ceased
- 1999-10-15 ES ES99952604T patent/ES2188260T3/es not_active Expired - Lifetime
- 1999-10-15 TR TR2001/01808T patent/TR200101808T2/xx unknown
- 1999-10-15 PL PL99347329A patent/PL195734B1/pl not_active IP Right Cessation
- 1999-10-15 DK DK99952604T patent/DK1121356T3/da active
- 1999-10-15 RU RU2001113272/04A patent/RU2222535C2/ru not_active IP Right Cessation
- 1999-10-15 DE DE69904849T patent/DE69904849T2/de not_active Expired - Lifetime
- 1999-10-15 JP JP2000577167A patent/JP4659984B2/ja not_active Expired - Fee Related
- 1999-10-15 BR BR9914582-0A patent/BR9914582A/pt active Search and Examination
- 1999-10-15 NZ NZ511289A patent/NZ511289A/xx not_active IP Right Cessation
- 1999-10-15 AT AT99952604T patent/ATE230741T1/de active
- 1999-10-15 CZ CZ20011353A patent/CZ20011353A3/cs unknown
- 1999-10-15 SI SI9930196T patent/SI1121356T1/xx unknown
- 1999-10-15 KR KR1020017004764A patent/KR100619464B1/ko not_active Expired - Fee Related
- 1999-10-15 UA UA2001053312A patent/UA66888C2/uk unknown
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- 1999-10-15 EP EP99952604A patent/EP1121356B1/fr not_active Expired - Lifetime
- 1999-10-16 DZ DZ990217A patent/DZ2917A1/fr active
2001
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Also Published As

Publication number	Publication date
HK1039333A1 (en)	2002-04-19
DZ2917A1 (fr)	2004-06-20
HUP0104701A2 (hu)	2002-04-29
ES2188260T3 (es)	2003-06-16
CA2346896A1 (fr)	2000-04-27
ATE230741T1 (de)	2003-01-15
AU750811B2 (en)	2002-07-25
PL195734B1 (pl)	2007-10-31
TR200101808T2 (tr)	2001-10-22
US6391896B1 (en)	2002-05-21
IL142589A (en)	2007-10-31
SK5122001A3 (en)	2001-10-08
JP4659984B2 (ja)	2011-03-30
IL142589A0 (en)	2002-03-10
EP1121356B1 (fr)	2003-01-08
NO20011892L (no)	2001-06-12
NO320531B1 (no)	2005-12-19
DK1121356T3 (da)	2003-03-24
PL347329A1 (en)	2002-03-25
NZ511289A (en)	2003-01-31
BR9914582A (pt)	2001-07-03
DE69904849T2 (de)	2003-11-13
WO2000023441A1 (fr)	2000-04-27
HUP0104701A3 (en)	2003-01-28
EP1121356A1 (fr)	2001-08-08
CN1140524C (zh)	2004-03-03
DE69904849D1 (de)	2003-02-13
CZ20011353A3 (cs)	2001-09-12
UA66888C2 (uk)	2004-06-15
CA2346896C (fr)	2008-12-09
KR20010080183A (ko)	2001-08-22
RU2222535C2 (ru)	2004-01-27
SK285764B6 (sk)	2007-07-06
NO20011892D0 (no)	2001-04-17
SI1121356T1 (en)	2003-04-30
JP2002527515A (ja)	2002-08-27
CN1328553A (zh)	2001-12-26
TW577884B (en)	2004-03-01
KR100619464B1 (ko)	2006-09-05
AR020773A1 (es)	2002-05-29
AU6474199A (en)	2000-05-08

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HUP9901016A2 (hu)	2000-03-28	4-Kinolinkarboxamid-származékok, előállításuk, valamint neurokinin-3 (NK-3) és neurokinin-2 (NK-2) receptor antagonistákként történő felhasználásuk
AU6538294A (en)	1994-11-08	Indole derivatives as 5-ht1a and/or 5-ht2 ligands
JP2005527463A (ja)	2005-09-15	Ｃｎｓ疾患を治療するための５−ｈｔ６受容体アフィニティーを有する３−アリールスルホニル−７−ピペラジニル−インドール、−ベンゾフランおよび−ベンゾチオフェン
WO1998006717A9 (fr)	1998-07-23	Indolecarboxamides fondus: ligands specifiques des sous-types de recepteur de la dopamine
WO2001014330A2 (fr)	2001-03-01	Nouvelles phenylpiperazines
ZA200103251B (en)	2002-07-22	3-Tetrahydropyridin-4-YL indoles for treatment of psychotic disorders.
EP1200072A2 (fr)	2002-05-02	Methode de traitement de troubles psychotiques
JP2007530648A (ja)	2007-11-01	Ｃｎｓ障害の処置のための、５−ｈｔ６受容体アンタゴニストとしての３−（（ヘテロ）アリールスルフォニル）−８−（（アミノアルキル）オキシ）キノリン
JP2001521935A (ja)	2001-11-13	３−アミノアルキルアミノ−２ｈ−１，４−ベンゾキシアジン及び３−アミノアルキルアミノ−２ｈ−１，４−ベンゾチアジン：ドーパミン受容体サブタイプ特定の配位子
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US6613901B2 (en)	2003-09-02	2-aminoalkylaminoquinolines as dopamine D4 ligands
US5972945A (en)	1999-10-26	2-aminoalkylaminoquinolines; dopamine receptor subtype specific ligands
HK1039333B (en)	2003-05-16	3-tetrahydropyridin-4-yl indoles for treatment of psychotic disorders
MXPA01003882A (es)	2002-06-05	3-tetrahidropiridin-4-il indoles para el tratamiento de trastornos psicoticos
FR2773800A1 (fr)	1999-07-23	Derives de benzimidazole, leur procede de preparation et leur application en therapeutique
CN101072770A (zh)	2007-11-14	对于多巴胺－d2受体和5－羟色胺再摄取位点具有联合亲和力的四氢吡啶－4－基吲哚
MXPA99010869A (en)	2000-06-01	2-aminoalkylaminoquinolines as dopamine d4