NO311027B1 - Alkylaminobenzotiazol og -benzoksazolderivater - Google Patents

Alkylaminobenzotiazol og -benzoksazolderivater Download PDF

Info

Publication number: NO311027B1
Authority: NO; Norway
Prior art keywords: formula; compound; compounds; alkyl; dopamine
Prior art date: 1996-05-10

Application number

NO19985227A

Other languages

English (en)

Norwegian (no)

Other versions

NO985227D0 (no

NO985227L (no

Inventor

Ludo Edmond Josephine Kennis

Josephus Carolus Mertens

Serge Maria Aloysius Pieters

Original Assignee

Janssen Pharmaceutica Nv

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.)

1996-05-10

Filing date

1998-11-09

Publication date

2001-10-01

1998-11-09 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1998-11-09 Publication of NO985227D0 publication Critical patent/NO985227D0/no

1999-01-11 Publication of NO985227L publication Critical patent/NO985227L/no

2001-10-01 Publication of NO311027B1 publication Critical patent/NO311027B1/no

Links

BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 129
239000000203 mixture Substances 0.000 claims description 60
239000002904 solvent Substances 0.000 claims description 41
102000003962 Dopamine D4 receptors Human genes 0.000 claims description 37
108090000357 Dopamine D4 receptors Proteins 0.000 claims description 37
238000000034 method Methods 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
239000000460 chlorine Substances 0.000 claims description 19
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
239000012442 inert solvent Substances 0.000 claims description 13
230000002285 radioactive effect Effects 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 10
230000003042 antagnostic effect Effects 0.000 claims description 9
239000002585 base Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
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238000003384 imaging method Methods 0.000 claims description 5
210000000056 organ Anatomy 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
239000012620 biological material Substances 0.000 claims description 4
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
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231100000252 nontoxic Toxicity 0.000 claims description 2
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AJYSDQBKCRYQNF-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenyl)piperazin-1-yl]propyl]-6-methoxy-1,3-benzothiazol-2-amine;dihydrochloride Chemical compound Cl.Cl.S1C2=CC(OC)=CC=C2N=C1NCCCN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 AJYSDQBKCRYQNF-UHFFFAOYSA-N 0.000 description 1
ODJJJYLWJQCPDH-UHFFFAOYSA-N n-[3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl]-1,3-benzothiazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCNC=3SC4=CC=CC=C4N=3)CC2)=C1 ODJJJYLWJQCPDH-UHFFFAOYSA-N 0.000 description 1
LUABFORHKKFGEL-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenyl)piperazin-1-yl]butyl]-6-methyl-1,3-benzothiazol-2-amine Chemical compound S1C2=CC(C)=CC=C2N=C1NCCCCN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 LUABFORHKKFGEL-UHFFFAOYSA-N 0.000 description 1
HVQAGCYLLHLDAE-UHFFFAOYSA-N n-[4-[4-(4-methoxyphenyl)piperazin-1-yl]butyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC(OC)=CC=C1N1CCN(CCCCNC=2SC3=CC=CC=C3N=2)CC1 HVQAGCYLLHLDAE-UHFFFAOYSA-N 0.000 description 1
AZCNTPSPOFJQJA-UHFFFAOYSA-N n-[5-[4-(3,4-dichlorophenyl)piperazin-1-yl]pentyl]-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(CCCCCNC=2SC3=CC=CC=C3N=2)CC1 AZCNTPSPOFJQJA-UHFFFAOYSA-N 0.000 description 1
OTISWVDIFYXZDC-WLHGVMLRSA-N n-benzyl-n-[5-[4-(3,4-dichlorophenyl)piperazin-1-yl]pentyl]-1,3-benzothiazol-2-amine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1=C(Cl)C(Cl)=CC=C1N1CCN(CCCCCN(CC=2C=CC=CC=2)C=2SC3=CC=CC=C3N=2)CC1 OTISWVDIFYXZDC-WLHGVMLRSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
229940054010 other antipsychotics in atc Drugs 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
208000022821 personality disease Diseases 0.000 description 1
238000000053 physical method Methods 0.000 description 1
206010036067 polydipsia Diseases 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
208000012201 sexual and gender identity disease Diseases 0.000 description 1
230000009329 sexual behaviour Effects 0.000 description 1
208000015891 sexual disease Diseases 0.000 description 1
238000003567 signal transduction assay Methods 0.000 description 1
238000002603 single-photon emission computed tomography Methods 0.000 description 1
230000007958 sleep Effects 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
238000003325 tomography Methods 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
- 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
- A61K31/42—Oxazoles
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO19985227A 1996-05-10 1998-11-09 Alkylaminobenzotiazol og -benzoksazolderivater NO311027B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP96201282		1996-05-10
PCT/EP1997/002505 WO1997043271A1 (en)	1996-05-10	1997-05-02	Alkylaminobenzothiazole and -benzoxazole derivatives

Publications (3)

Publication Number	Publication Date
NO985227D0 NO985227D0 (no)	1998-11-09
NO985227L NO985227L (no)	1999-01-11
NO311027B1 true NO311027B1 (no)	2001-10-01

Family

ID=8223970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19985227A NO311027B1 (no)	1996-05-10	1998-11-09	Alkylaminobenzotiazol og -benzoksazolderivater

Country Status (28)

Country	Link
US (2)	US6103725A (cs)
EP (2)	EP1325917B1 (cs)
JP (1)	JP3237759B2 (cs)
KR (1)	KR100330699B1 (cs)
CN (1)	CN1074766C (cs)
AR (1)	AR007079A1 (cs)
AT (2)	ATE350373T1 (cs)
AU (1)	AU710175B2 (cs)
BG (1)	BG64097B1 (cs)
BR (1)	BR9709065A (cs)
CA (1)	CA2253453C (cs)
CZ (1)	CZ295639B6 (cs)
DE (2)	DE69730962T2 (cs)
EA (1)	EA001360B1 (cs)
EE (1)	EE03563B1 (cs)
ES (2)	ES2230605T3 (cs)
HU (1)	HUP9902993A3 (cs)
ID (1)	ID16889A (cs)
IL (1)	IL126968A0 (cs)
MY (1)	MY117852A (cs)
NO (1)	NO311027B1 (cs)
NZ (1)	NZ332309A (cs)
PL (1)	PL190721B1 (cs)
SK (1)	SK282919B6 (cs)
TR (1)	TR199802253T2 (cs)
TW (1)	TW593290B (cs)
WO (1)	WO1997043271A1 (cs)
ZA (1)	ZA974053B (cs)

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IT1293804B1 (it)	1997-08-01	1999-03-10	Recordati Chem Pharm	Diarilalchilpiperazine attive sulle basse vie urinarie
US6281216B1 (en) *	1998-02-09	2001-08-28	Duphar International Research B.V.	2-aminoquinoline derivatives having d4-agonistic activity
EP0982030A3 (en)	1998-08-17	2000-05-10	Pfizer Products Inc.	2,7-substituted octahydro-pyrrolo 1,2-a]pyrazine derivatives as 5ht 1a ligands
AU6280199A (en) *	1998-09-30	2000-04-17	Neurogen Corporation	2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands
US6284759B1 (en) *	1998-09-30	2001-09-04	Neurogen Corporation	2-piperazinoalkylaminobenzo-azole derivatives: dopamine receptor subtype specific ligands
US6107313A (en) *	1998-10-02	2000-08-22	Combichem, Inc.	Dopamine receptor antagonists
AU5569800A (en) *	1999-06-30	2001-01-31	Santen Pharmaceutical Co. Ltd.	Brain sigma-1 receptor-binding ligand
ATE361297T1 (de)	2000-03-31	2007-05-15	Ortho Mcneil Pharm Inc	Phenyl-substituierte imidazopyridine
US6436939B2 (en)	2000-03-31	2002-08-20	Ortho-Mcneil Pharmaceutical, Inc.	Method for using 2-aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles as H3 antagonists
GB0203299D0 (en) *	2002-02-12	2002-03-27	Glaxo Group Ltd	Novel compounds
PL377087A1 (pl)	2002-09-06	2006-01-23	Janssen Pharmaceutica, N.V.	Związki heterocykliczne
EP2610234A1 (en) *	2004-02-24	2013-07-03	The General Hospital Corporation	Catalytic radiofluorination
US8257680B1 (en)	2004-02-24	2012-09-04	The General Hospital Corporation	Catalytic radiofluorination
US9017724B2 (en)	2004-02-24	2015-04-28	The General Hospital Corporation	Catalytic radiofluorination
FR2877005A1 (fr) *	2004-10-22	2006-04-28	Bioprojet Soc Civ Ile	Nouveaux derives d'arylpiperazine
US7731940B2 (en)	2006-01-25	2010-06-08	The Regents Of The University Of California	Compositions and methods related to serotonin 5-HT1A receptors
EP3231804B1 (en)	2008-03-21	2021-03-03	The General Hospital Corporation	Compounds and compositions for the detection and treatment of alzheimer's disease and related disorders
US11337970B2 (en) *	2016-08-26	2022-05-24	Bristol-Myers Squibb Company	Inhibitors of indoleamine 2,3-dioxygenase and methods of their use
PT109740B (pt)	2016-11-14	2020-07-30	Hovione Farmaciencia Sa	Processo para a preparação de brometo de umeclidínio
KR102823891B1 (ko) *	2020-01-14	2025-06-20	서울대학교산학협력단	혈관생성 저해 효과를 가지는 n-페닐벤조티아졸-2-아민 화합물 및 그를 포함하는 약제학적 조성물
CN116730948A (zh) *	2022-03-02	2023-09-12	圣奥化学科技有限公司	一种合成n-环己基-2-苯并噻唑的方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0187162B1 (en) *	1984-05-22	1989-11-02	Sumitomo Chemical Company, Limited	Novel radioactive iodospiroperidol and process for its preparation
DE3874187T2 (de) *	1987-04-08	1993-04-08	Salutar Inc	Nachweis fuer amyloidose und alzheimer'sche krankheit sowie reagens hierfuer.
US4929618A (en) *	1988-03-25	1990-05-29	Ube Industries, Ltd.	Piperdine and piperazine derivatives, and antihistaminic pharmaceutical compositions containing the same
FR2656609B1 (fr) *	1989-12-28	1992-03-27	Synthelabo	Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique.
US5731438A (en) *	1996-08-01	1998-03-24	Isis Pharmaceuticals, Inc.	N-(aminoalkyl)-and/or N-(amidoalkyl)-dinitrogen heterocycles

1997
- 1997-05-01 TW TW086105767A patent/TW593290B/zh not_active IP Right Cessation
- 1997-05-02 EP EP03075959A patent/EP1325917B1/en not_active Expired - Lifetime
- 1997-05-02 CN CN97194515A patent/CN1074766C/zh not_active Expired - Lifetime
- 1997-05-02 CZ CZ19983553A patent/CZ295639B6/cs not_active IP Right Cessation
- 1997-05-02 US US09/180,369 patent/US6103725A/en not_active Expired - Lifetime
- 1997-05-02 NZ NZ332309A patent/NZ332309A/xx unknown
- 1997-05-02 DE DE69730962T patent/DE69730962T2/de not_active Expired - Lifetime
- 1997-05-02 ES ES97923913T patent/ES2230605T3/es not_active Expired - Lifetime
- 1997-05-02 IL IL12696897A patent/IL126968A0/xx not_active IP Right Cessation
- 1997-05-02 AU AU29560/97A patent/AU710175B2/en not_active Ceased
- 1997-05-02 TR TR1998/02253T patent/TR199802253T2/xx unknown
- 1997-05-02 SK SK1532-98A patent/SK282919B6/sk not_active IP Right Cessation
- 1997-05-02 AT AT03075959T patent/ATE350373T1/de not_active IP Right Cessation
- 1997-05-02 EP EP97923913A patent/EP0912533B1/en not_active Expired - Lifetime
- 1997-05-02 ES ES03075959T patent/ES2279923T3/es not_active Expired - Lifetime
- 1997-05-02 PL PL97329849A patent/PL190721B1/pl not_active IP Right Cessation
- 1997-05-02 WO PCT/EP1997/002505 patent/WO1997043271A1/en not_active Ceased
- 1997-05-02 EA EA199801000A patent/EA001360B1/ru not_active IP Right Cessation
- 1997-05-02 EE EE9800378A patent/EE03563B1/xx not_active IP Right Cessation
- 1997-05-02 KR KR1019980707914A patent/KR100330699B1/ko not_active Expired - Fee Related
- 1997-05-02 CA CA002253453A patent/CA2253453C/en not_active Expired - Fee Related
- 1997-05-02 JP JP54053597A patent/JP3237759B2/ja not_active Expired - Lifetime
- 1997-05-02 HU HU9902993A patent/HUP9902993A3/hu unknown
- 1997-05-02 DE DE69737217T patent/DE69737217T2/de not_active Expired - Lifetime
- 1997-05-02 BR BR9709065A patent/BR9709065A/pt not_active IP Right Cessation
- 1997-05-02 AT AT97923913T patent/ATE277917T1/de not_active IP Right Cessation
- 1997-05-07 MY MYPI97002022A patent/MY117852A/en unknown
- 1997-05-09 AR ARP970101955A patent/AR007079A1/es active IP Right Grant
- 1997-05-09 ID IDP971546A patent/ID16889A/id unknown
- 1997-05-09 ZA ZA974053A patent/ZA974053B/xx unknown
1998
- 1998-10-07 BG BG102819A patent/BG64097B1/bg unknown
- 1998-11-09 NO NO19985227A patent/NO311027B1/no unknown
2000
- 2000-06-27 US US09/604,427 patent/US6224849B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ID16889A (id)	1997-11-20
SK153298A3 (en)	1999-03-12
TW593290B (en)	2004-06-21
CN1074766C (zh)	2001-11-14
DE69730962D1 (de)	2004-11-04
DE69737217D1 (de)	2007-02-15
CZ295639B6 (cs)	2005-09-14
HUP9902993A3 (en)	2002-01-28
US6224849B1 (en)	2001-05-01
CA2253453C (en)	2007-01-16
EE03563B1 (et)	2001-12-17
CZ355398A3 (cs)	1999-02-17
BG102819A (en)	1999-08-31
AU710175B2 (en)	1999-09-16
BG64097B1 (bg)	2003-12-31
EA001360B1 (ru)	2001-02-26
HK1057044A1 (en)	2004-03-12
KR20000005227A (ko)	2000-01-25
ES2230605T3 (es)	2005-05-01
ZA974053B (en)	1998-11-09
NO985227D0 (no)	1998-11-09
DE69730962T2 (de)	2006-03-30
EP1325917B1 (en)	2007-01-03
WO1997043271A1 (en)	1997-11-20
PL329849A1 (en)	1999-04-12
KR100330699B1 (ko)	2002-08-27
AU2956097A (en)	1997-12-05
ATE350373T1 (de)	2007-01-15
EP0912533A1 (en)	1999-05-06
ATE277917T1 (de)	2004-10-15
IL126968A0 (en)	1999-09-22
JP3237759B2 (ja)	2001-12-10
EP1325917A1 (en)	2003-07-09
NO985227L (no)	1999-01-11
BR9709065A (pt)	1999-08-03
EA199801000A1 (ru)	1999-04-29
ES2279923T3 (es)	2007-09-01
MY117852A (en)	2004-08-30
EP0912533B1 (en)	2004-09-29
AR007079A1 (es)	1999-10-13
HUP9902993A2 (hu)	2000-05-28
HK1018457A1 (en)	1999-12-24
SK282919B6 (sk)	2003-01-09
CN1218461A (zh)	1999-06-02
NZ332309A (en)	1999-08-30
PL190721B1 (pl)	2005-12-30
JP2000503667A (ja)	2000-03-28
DE69737217T2 (de)	2007-11-08
EE9800378A (et)	1999-04-15
CA2253453A1 (en)	1997-11-20
TR199802253T2 (xx)	1999-02-22
US6103725A (en)	2000-08-15

Publication	Publication Date	Title
NO311027B1 (no)	2001-10-01	Alkylaminobenzotiazol og -benzoksazolderivater
EP0912552B1 (en)	2004-04-21	2,4-diaminopyrimidine derivates as dopamine d4 receptor antagonists
CZ2000726A3 (cs)	2000-07-12	Tetrahydro-gama-karboliny a způsob jejich přípravy
US5919784A (en)	1999-07-06	Heterocyclic aminomethyl compounds
JP4590102B2 (ja)	2010-12-01	医薬としての三環性δ３−ピペリジン類
JP2008509962A (ja)	2008-04-03	５−ｈｔ７受容体アンタゴニスト
JP2008509961A (ja)	2008-04-03	５−ｈｔ７受容体アンタゴニスト
JP4580555B2 (ja)	2010-11-17	α２アンタゴニストとしてのベンゾチエノ［３，２−ｃ］ピリジン類
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