SK5082001A3 - Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907 - Google Patents

Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907 Download PDF

Info

Publication number: SK5082001A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; carbon atoms; patient; ethyl
Prior art date: 1998-10-14

Application number

SK508-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Albert A Carr

Hijfte Luc E Van

Raymond W Kosley Jr

Original Assignee

Aventis Pharma Inc

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.)

1998-10-14

Filing date

1998-10-14

Publication date

2001-11-06

1998-10-14 Application filed by Aventis Pharma Inc filed Critical Aventis Pharma Inc

2001-11-06 Publication of SK5082001A3 publication Critical patent/SK5082001A3/sk

Links

HXTGXYRHXAGCFP-UHFFFAOYSA-N volinanserin Chemical compound COC1=CC=CC(C(O)C2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1OC HXTGXYRHXAGCFP-UHFFFAOYSA-N 0.000 title abstract description 20
150000002148 esters Chemical class 0.000 title abstract description 7
239000002400 serotonin 2A antagonist Substances 0.000 title description 4
229940002612 prodrug Drugs 0.000 title description 2
239000000651 prodrug Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 101
238000000034 method Methods 0.000 claims abstract description 54
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 24
208000028017 Psychotic disease Diseases 0.000 claims abstract description 20
230000000694 effects Effects 0.000 claims abstract description 19
201000000980 schizophrenia Diseases 0.000 claims abstract description 12
229940076279 serotonin Drugs 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
239000003921 oil Substances 0.000 claims description 32
235000019198 oils Nutrition 0.000 claims description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
230000008569 process Effects 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 12
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NRZSFXSGLNDVSL-UHFFFAOYSA-N [(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methyl] decanoate Chemical compound C=1C=CC(OC)=C(OC)C=1C(OC(=O)CCCCCCCCC)C(CC1)CCN1CCC1=CC=C(F)C=C1 NRZSFXSGLNDVSL-UHFFFAOYSA-N 0.000 claims description 8
230000003042 antagnostic effect Effects 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
208000020925 Bipolar disease Diseases 0.000 claims description 7
150000001266 acyl halides Chemical class 0.000 claims description 7
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150000008065 acid anhydrides Chemical class 0.000 claims description 6
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230000009471 action Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
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206010002383 Angina Pectoris Diseases 0.000 claims description 3
235000019483 Peanut oil Nutrition 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
239000000312 peanut oil Substances 0.000 claims description 3
235000019489 Almond oil Nutrition 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
FZWNGWQLLKVBAT-UHFFFAOYSA-N [(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methyl] hexanoate Chemical compound C=1C=CC(OC)=C(OC)C=1C(OC(=O)CCCCC)C(CC1)CCN1CCC1=CC=C(F)C=C1 FZWNGWQLLKVBAT-UHFFFAOYSA-N 0.000 claims description 2
MLFSJKBJROALNB-UHFFFAOYSA-N [(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methyl] octanoate Chemical compound C=1C=CC(OC)=C(OC)C=1C(OC(=O)CCCCCCC)C(CC1)CCN1CCC1=CC=C(F)C=C1 MLFSJKBJROALNB-UHFFFAOYSA-N 0.000 claims description 2
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
239000004359 castor oil Substances 0.000 claims description 2
235000019438 castor oil Nutrition 0.000 claims description 2
239000002285 corn oil Substances 0.000 claims description 2
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230000000994 depressogenic effect Effects 0.000 claims description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
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125000001309 chloro group Chemical group Cl* 0.000 claims 4
229940125898 compound 5 Drugs 0.000 claims 2
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WAUXROZRQSIOBJ-UHFFFAOYSA-N [(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methyl] 2,2-dimethyloctanoate Chemical compound C=1C=CC(OC)=C(OC)C=1C(OC(=O)C(C)(C)CCCCCC)C(CC1)CCN1CCC1=CC=C(F)C=C1 WAUXROZRQSIOBJ-UHFFFAOYSA-N 0.000 claims 1
DEPYAHKFIJUDNY-UHFFFAOYSA-N [(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methyl] hexadecanoate Chemical compound C=1C=CC(OC)=C(OC)C=1C(OC(=O)CCCCCCCCCCCCCCC)C(CC1)CCN1CCC1=CC=C(F)C=C1 DEPYAHKFIJUDNY-UHFFFAOYSA-N 0.000 claims 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 70
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
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239000005720 sucrose Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 17
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
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HXTGXYRHXAGCFP-OAQYLSRUSA-N (r)-(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methanol Chemical compound COC1=CC=CC([C@H](O)C2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1OC HXTGXYRHXAGCFP-OAQYLSRUSA-N 0.000 description 14
241000700159 Rattus Species 0.000 description 14
238000004458 analytical method Methods 0.000 description 13
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 12
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239000012267 brine Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
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229910002027 silica gel Inorganic materials 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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239000003480 eluent Substances 0.000 description 11
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BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 7
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FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
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JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Addiction (AREA)
Epidemiology (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK508-2001A 1998-10-14 1998-10-14 Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907 SK5082001A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1998/021608 WO2000021930A1 (en)	1998-10-14	1998-10-14	Esters of (+)-alpha-( 2,3- dimethoxyphenyl) -1-[2-(4- fluorophenyl) ethyl]-4- piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907

Publications (1)

Publication Number	Publication Date
SK5082001A3 true SK5082001A3 (en)	2001-11-06

Family

ID=22268079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK508-2001A SK5082001A3 (en)	1998-10-14	1998-10-14	Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907

Country Status (20)

Country	Link
EP (1)	EP1121345A1 (cs)
JP (1)	JP2002527422A (cs)
KR (1)	KR100515429B1 (cs)
CN (1)	CN1160333C (cs)
AU (1)	AU1083099A (cs)
BR (1)	BR9816049A (cs)
CA (1)	CA2347469C (cs)
CZ (1)	CZ20011331A3 (cs)
EA (1)	EA003667B1 (cs)
EE (1)	EE200100219A (cs)
HR (1)	HRP20010278A2 (cs)
HU (1)	HUP0200517A3 (cs)
IL (2)	IL142479A0 (cs)
NO (1)	NO320417B1 (cs)
NZ (1)	NZ510631A (cs)
PL (1)	PL193306B1 (cs)
SK (1)	SK5082001A3 (cs)
TR (1)	TR200101047T2 (cs)
UA (1)	UA57859C2 (cs)
WO (1)	WO2000021930A1 (cs)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20020099076A1 (en) *	2000-05-25	2002-07-25	Richard Scheyer D.	Use of (+)-a-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol or its prodrug in the treatment of symptoms of dementia and dopamine induced psychosis
CN102241667B (zh) *	2010-05-14	2013-10-23	中国人民解放军军事医学科学院毒物药物研究所	1-[(4-羟基哌啶-4基)甲基]吡啶-2(1h)-酮衍生物及其制备方法和用途
CN106892897A (zh) *	2015-12-21	2017-06-27	上海科胜药物研发有限公司	一种羟哌吡酮游离碱新晶型及其制备方法
CN106928187A (zh) *	2015-12-31	2017-07-07	上海奥博生物医药技术有限公司	一种盐酸羟哌吡酮新晶型及其制备方法
US20220273628A1 (en) *	2021-02-19	2022-09-01	Universitätsspital Basel	Effects of lysergic acid diethylamide (lsd) and of lsd analogs to assist psychotherapy for generalized anxiety disorder or other anxiety not related to life-threatening illness
EP4329759A4 (en)	2021-04-30	2025-07-16	Mind Medicine Inc	CRYSTALLINE FORMS OF LSD SALTS
JP7846211B2 (ja)	2021-08-19	2026-04-14	デフィニウムセラピューティクスユーエス，インコーポレイテッド	治療適用のためのｄ－リゼルグ酸ジエチルアミドの即時放出製剤

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2083698C (en) *	1990-06-01	1997-11-04	Albert A. Carr	(+)-alpha-(2,3-dimethoxyphenyl)-1- [2-(4-fluorophenyl) ethyl]-4-piperidinemethanol

1998
- 1998-10-14 CA CA002347469A patent/CA2347469C/en not_active Expired - Fee Related
- 1998-10-14 IL IL14247998A patent/IL142479A0/xx active IP Right Grant
- 1998-10-14 EA EA200100361A patent/EA003667B1/ru not_active IP Right Cessation
- 1998-10-14 BR BR9816049-4A patent/BR9816049A/pt not_active Application Discontinuation
- 1998-10-14 CZ CZ20011331A patent/CZ20011331A3/cs unknown
- 1998-10-14 JP JP2000575839A patent/JP2002527422A/ja active Pending
- 1998-10-14 NZ NZ510631A patent/NZ510631A/en active IP Right Revival
- 1998-10-14 CN CNB988142740A patent/CN1160333C/zh not_active Expired - Fee Related
- 1998-10-14 HR HR20010278A patent/HRP20010278A2/hr not_active Application Discontinuation
- 1998-10-14 HU HU0200517A patent/HUP0200517A3/hu unknown
- 1998-10-14 TR TR2001/01047T patent/TR200101047T2/xx unknown
- 1998-10-14 AU AU10830/99A patent/AU1083099A/en not_active Abandoned
- 1998-10-14 WO PCT/US1998/021608 patent/WO2000021930A1/en not_active Ceased
- 1998-10-14 KR KR10-2001-7004703A patent/KR100515429B1/ko not_active Expired - Fee Related
- 1998-10-14 EE EEP200100219A patent/EE200100219A/xx unknown
- 1998-10-14 PL PL347318A patent/PL193306B1/pl not_active IP Right Cessation
- 1998-10-14 EP EP98953458A patent/EP1121345A1/en not_active Withdrawn
- 1998-10-14 SK SK508-2001A patent/SK5082001A3/sk not_active Application Discontinuation
- 1998-10-14 UA UA2001042522A patent/UA57859C2/uk unknown
2001
- 2001-04-05 IL IL142479A patent/IL142479A/en not_active IP Right Cessation
- 2001-04-09 NO NO20011805A patent/NO320417B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA2347469C (en)	2006-02-28
KR20010106517A (ko)	2001-11-29
HK1039332A1 (en)	2002-04-19
PL193306B1 (pl)	2007-01-31
CA2347469A1 (en)	2000-04-20
IL142479A0 (en)	2002-03-10
CN1160333C (zh)	2004-08-04
IL142479A (en)	2006-06-11
NO20011805L (no)	2001-06-08
NO320417B1 (no)	2005-12-05
NO20011805D0 (no)	2001-04-09
CZ20011331A3 (cs)	2001-08-15
CN1314887A (zh)	2001-09-26
TR200101047T2 (tr)	2001-08-21
EA200100361A1 (ru)	2001-10-22
PL347318A1 (en)	2002-03-25
AU1083099A (en)	2000-05-01
UA57859C2 (uk)	2003-07-15
HRP20010278A2 (en)	2002-06-30
WO2000021930A1 (en)	2000-04-20
EP1121345A1 (en)	2001-08-08
HUP0200517A2 (en)	2002-06-29
JP2002527422A (ja)	2002-08-27
EA003667B1 (ru)	2003-08-28
NZ510631A (en)	2003-07-25
BR9816049A (pt)	2001-07-03
HUP0200517A3 (en)	2002-12-28
KR100515429B1 (ko)	2005-09-20
EE200100219A (et)	2002-08-15

Legal Events

Date	Code	Title	Description
2010-02-08	FC9A	Refused patent application

Publication	Publication Date	Title
US6028083A (en)	2000-02-22	Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol
EP1289527B1 (en)	2008-03-26	(+)-alpha-(2,3-dimethoxyphenyl)-1(2-(4-fluorophenyl)ethyl)-4-piperidinemethanol or its prodrug to treat dementia or cognitive impairment
SK5082001A3 (en)	2001-11-06	Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907
TW517048B (en)	2003-01-11	Pharmaceutical composition for treating depressive disorders and bipolardisorders comprising (+)-Α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
AU2001264842A1 (en)	2002-02-21	Use of (+)-alpha -(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)-4- piperidinemerthanol or its prodrug in the treatment of symptoms of dementia and dopamine induced psychosis
US6939879B2 (en)	2005-09-06	Use of R (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol for the treatment of substance induced insomnia
AU2004200993A1 (en)	2004-04-01	Esters of (+)-alpha-(2,3-dimethoxyphenyl-[2-(4-flurophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5HT2a receptor antagonist MDL 110,907
BG65206B1 (bg)	2007-07-31	Естери на (+)-алфа-(2,3-диметоксифенил)-1-[2-(4-флуорoфенил)етил]-4- пиперидинметанол, метод за тяхното получаване и приложението им като предшественици на 5ht2a рецепторния антагонист mdl 110,907
MXPA01003535A (en)	2002-06-05	Esters of (+)-alpha-( 2,3- dimethoxyphenyl) -1-[2-(4- fluorophenyl) ethyl]-4- piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907
EP1362589B1 (en)	2009-07-15	Use of R(+)-alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)-4- piperidinemethanol for the treatment of sleep disorders
TW461885B (en)	2001-11-01	Esters of (+)-Α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
HK1039332B (en)	2005-02-04	Piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907
PL203533B1 (pl)	2009-10-30	Zastosowanie (+)- a-(2,3-dimetoksyfenylo)-1-[2-(4-fluorofenylo)etylo]-4-piperydynometanolu lub jego proleku