FI113862B - Förfarande för framställning av nya terapeutiskt användbara 1-piperazino-1,2-dihydroindenderivat - Google Patents

Förfarande för framställning av nya terapeutiskt användbara 1-piperazino-1,2-dihydroindenderivat Download PDF

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FI113862B
FI113862B FI945042A FI945042A FI113862B FI 113862 B FI113862 B FI 113862B FI 945042 A FI945042 A FI 945042A FI 945042 A FI945042 A FI 945042A FI 113862 B FI113862 B FI 113862B
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hydrogen
compound
formula
lower alkyl
ring
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FI945042A
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FI945042A0 (sv
FI945042A (sv
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Klaus Boegesoe
Peter Bregnedal
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Lundbeck & Co As H
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • 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
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Neurosurgery (AREA)
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  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Claims (3)

1. Förfarande för framställning av nya terapeutiskt användbara transisomerer av 1-piperazino-l,2-dihydroinden-5 föreningar med formeln I och farmaceutiskt godtagbara syra-additionssalter därav, R3. F>2 x yps. N N— R i Y_c |i f V[_y (i) R4 Ar i vilken formel X och Y betecknar oberoende av varandra väte, halogen, trifluormetyl, lägre alkyl eller nitro; Ar är 10 en fenylgrupp, en fenylgrupp, som är substituerad med en eller flera substituenter, som är halogen, eller Ar är en tienylgrupp; Ri är väte eller lägre alkyl, som kan vara substituerad med en hydroxigrupp; R2 är lägre alkyl; eller Ri och R2 bildar tillsammans med kväve- och kolatomerna, 15 tili vilka de är bundna, en 5 - 7 -ledad heterocyklisk ring, som är fusionerad med piperazinringen och som kan va-d ra substituerad med hydroxi; Γ R3 är väte eller lägre alkyl; eller R2 ja R3 bildar tillsammans med kolatomen, tili vilken de är bundna, en 3 -: 20 7-ledad karbocyklisk ring, som är spirobunden tili pipera- ;· zinringen; och R4 är väte eller lägre alkyl; t förutsatt, att R2 och R3, ej bildar en ring, da Ri och R2 tillsammans bildar en ring; kännetecknat därav, att 7! 25 a) en förening med formeln !i# Y (II) <.: Ar * I 113862 33 behandlas med ett piperazinderivat med formeln "V2 /' _ (III) HN n— Rf r4 i vilka formler X, Y, Ar,Ri, R2, R3 och R4 betecknar sarana 5 som ovan och Z är halogen eller -0S02R6, där Re är alkyl, säsom CH3, eller aryl, säsom p-toluoyl; eller b) en förening med formeln vRz ,>wV" R< Ar där X, Y , Ar, R2,R-3 och R4 betecknar samma som ovan, be- 10 handlas med en förening med formeln Ri-Z, där Rx och Z be- , . tecknar samma som ovan, förutom att Rx ej är väte, eller med en epoxid, med CH2—ch R' formeln · \ / * 0 där R' är väte, metyl eller etyl; eller • 15 c) en förening med formeln IV behandlas med en fö- ;* rening med formeln R’’-CHO, där R'' är väte eller C1-C3- ; alkyl, i närvaro av ett reduktionsmedel; eller d) en förening med formeln IV behandlas med HCHO/HCOOH, varvid erhälls en förening med formeln I, där *, 20 Ri är metyl (Enschweiler-Clarke-metylering); eller e) en förening med formeln * · Rn Q x ^2 . N NCOR' ;; Οςτ y Ar 113862 34 där X, Y, Ar,R2,R3, och R4 betecknar sainma som ovan och R' är väte eller Ci-C3-alkyl, reduceras; eller f) en förening med formeln x AR2 ^ N N— D. (vi) Όςτν Ar 5 där X, Y, Ar, R2, R3 och R4 betecknar sainma som ovan och R'1 innehäller en ester-, keton- eller aldehydgrupp, reduceras med ett lämpligt reduktionsmedel tili en motsvarande förening, som innehäller en hydroxigrupp.
2. Förfarande enligt patentkrav 1, kanne-10 tecknat därav, att man framställer en förening med formeln I, där X är väte, halogen, lägre alkyl eller tri-fluormetyl; Y är väte eller halogen; Ar är fenyl, fenyl, som är substituerad med halo-15 gen, eller Ar är tienyl; , , Ri är väte, lägre alkyl eller lägre alkyl, som är > · substituerad med hydroxi; : R2 är lägre alkyl, eller .· Ri och R2 bildar tillsammans med kväve- och kolato- I 20 merna, tili vilka de är bundna, en piperidinoring, som är ;· fusionerad med piperazinringen och som kan vara substitue- rad med hydroxi; R3 är väte eller lägre alkyl, eller R2 och R3 bil-dar tillsammans med kolatomen, tili vilken de är bundna, !! 25 en spirocykloalkylring; och 1' R4 är väte eller metyl.
3. Förfarande enligt patentkrav 1, k ä n n e -tecknat därav, att man framställer en förening med formeln I, där I I . 30 X är en väte-, klor-, brom-, eller fluoratom, me tyl eller trifluormetyl; Y är väte; 113862 35 Ar är fenyl fluorfenyl eller tienyl; Ri är väte, metyl, 2-propyl, hydroxipropyl eller hydroxietyl; R2 ar CH3, etyl eller 2-propyl och R3 är H, etyl 5 eller metyl eller R2 och R3 bildar tillsammans med kolato-men, till vilken de är bundna, en spirocyklobutan- eller spirocyklopentylring; och R4 är väte. * · 1 ·
FI945042A 1992-04-28 1994-10-26 Förfarande för framställning av nya terapeutiskt användbara 1-piperazino-1,2-dihydroindenderivat FI113862B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DK92551A DK55192D0 (da) 1992-04-28 1992-04-28 1-piperazino-1,2-dihydroindenderivater
DK55192 1992-04-28
PCT/DK1993/000136 WO1993022293A1 (en) 1992-04-28 1993-04-23 1-piperazino-1,2-dihydroindene derivatives
DK9300136 1993-04-23

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FI945042A0 FI945042A0 (sv) 1994-10-26
FI945042A FI945042A (sv) 1994-10-26
FI113862B true FI113862B (sv) 2004-06-30

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US (1) US5807855A (sv)
EP (1) EP0638073B1 (sv)
JP (1) JP3255416B2 (sv)
KR (1) KR100267635B1 (sv)
AT (1) ATE194003T1 (sv)
AU (1) AU669709B2 (sv)
CA (1) CA2134566C (sv)
CL (1) CL2003002050A1 (sv)
CZ (1) CZ281676B6 (sv)
DE (1) DE69328901T2 (sv)
DK (2) DK55192D0 (sv)
ES (1) ES2148227T3 (sv)
FI (1) FI113862B (sv)
GR (1) GR3034396T3 (sv)
HK (1) HK1013816A1 (sv)
HU (2) HUT71419A (sv)
IL (1) IL105464A (sv)
NO (1) NO306946B1 (sv)
NZ (1) NZ252098A (sv)
PT (1) PT638073E (sv)
RU (1) RU2114106C1 (sv)
SK (1) SK281613B6 (sv)
WO (1) WO1993022293A1 (sv)
ZA (1) ZA932840B (sv)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6251893B1 (en) * 1998-06-15 2001-06-26 Nps Allelix Corp. Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity
KR100849839B1 (ko) * 2001-02-23 2008-08-01 머크 앤드 캄파니 인코포레이티드 Ｎ-치환된 비-아릴-헤테로사이클릭 ｎｍｄａ/ｎｒ2ｂ 길항제 및 이를 포함하는 약제학적 조성물
CN1606552A (zh) 2001-12-21 2005-04-13 H.隆德贝克有限公司 氨基茚满衍生物作为5－羟色胺和去甲肾上腺素摄取抑制剂
IS7282A (is) * 2001-12-21 2004-05-21 H. Lundbeck A/S Amínóindan afleiður sem serótónín og noradrenalínupptökuhindrar
PL199016B1 (pl) † 2002-06-20 2008-08-29 Adamed Sp Z Oo Sposób wytwarzania olanzapiny
DE10334188B4 (de) * 2003-07-26 2007-07-05 Schwarz Pharma Ag Verwendung von Rotigotin zur Behandlung von Depressionen
DE10334187A1 (de) * 2003-07-26 2005-03-03 Schwarz Pharma Ag Substituierte 2-Aminotetraline zur Behandlung von Depressionen
EA200600443A1 (ru) * 2003-08-18 2006-08-25 Х. Лундбекк А/С Транс-1-(6-хлор-3-фенилиндан-1-ил)-3,3-диметилпиперазин
US7767683B2 (en) 2003-08-18 2010-08-03 H. Lundbeck A/S Hydrogen succinate salts of trans-4-((1R, 3S)-6-chloro-3-phenylindan-1-YL)-1,2,2-trimethylpiperazine and the use as a medicament
DE10361258A1 (de) * 2003-12-24 2005-07-28 Schwarz Pharma Ag Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson
US20050197385A1 (en) * 2004-02-20 2005-09-08 Schwarz Pharma Ag Use of rotigotine for treatment or prevention of dopaminergic neuron loss
DE102004014841B4 (de) * 2004-03-24 2006-07-06 Schwarz Pharma Ag Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms
TWI453198B (zh) * 2005-02-16 2014-09-21 Lundbeck & Co As H 製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s）-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法
JP2008530039A (ja) * 2005-02-16 2008-08-07 ハー・ルンドベック・アクチエゼルスカベット トランス−１−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−３，３−ジメチルピペラジンの酒石酸塩およびリンゴ酸塩
TWI376373B (en) * 2005-02-16 2012-11-11 Lundbeck & Co As H Crystalline base of a pharmaceutical compound
TW200819426A (en) 2006-08-31 2008-05-01 Lundbeck & Co As H Novel indane compounds
KR20110021754A (ko) * 2008-05-07 2011-03-04 하. 룬드벡 아크티에셀스카브 인지 결함 치료 방법
CA2732613A1 (en) * 2008-10-03 2010-04-08 H. Lundbeck A/S Oral formulation
ES2536779T3 (es) * 2009-04-30 2015-05-28 Abbvie Deutschland Gmbh & Co Kg Compuestos de N-fenil-(piperazinil u homopiperazinil)-bencensulfonamida o bencensulfonil-fenil-(piperazina u homopiperazina) adecuados para tratar trastornos que responden a la modulación del receptor de serotonina 5-HT6
TW201102370A (en) 2009-07-07 2011-01-16 Lundbeck & Co As H Manufacture of 4-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl piperazine
DK2639216T3 (en) 2010-11-09 2018-09-24 Kaneka Corp Halogenated Indones and Methods for Preparation of Optically Active Indanones or Optically Active Indanols Using These
CA2823103A1 (en) * 2011-01-07 2012-07-12 H. Lundbeck A/S Method for resolution of 4-((1r,3s)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1r,3s)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl-piperazine
PE20141113A1 (es) 2011-06-20 2014-09-25 Lundbeck & Co As H 1-piperazino-3-fenil-indanos deuterados para el tratamiento de esquizofrenia
JO3421B1 (ar) 2011-06-20 2019-10-20 H Lundbeck As طريقة لإعطاء 1-((1ار.3س)-6-كلورو-3-فينيل-اندان-1-ايل)-1.2.2-ترايميثيل- بيبيرازين واملاجها لمعالجة انفصام الشخصية
WO2019193134A1 (en) * 2018-04-06 2019-10-10 H. Lundbeck A/S Process for the preparation of 2,2-dimethylpiperazine
JP7442538B2 (ja) 2018-10-29 2024-03-04 ハー・ルンドベック・アクチエゼルスカベット 非晶性の式（ｉ）の化合物及び非晶性の式（ｉ）の化合物塩
CN113056457A (zh) 2018-12-03 2021-06-29 H.隆德贝克有限公司 4-((1R,3S)-6-氯-3-苯基-2,3-二氢-1H-茚-1-基)-1,2,2-三甲基哌嗪和4-((1R,3S)-6-氯-3-(苯基-d5)-2,3-二氢-1H-茚-1-基)-2,2-二甲基-1-(甲基-d3)哌嗪的前药

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4038395A (en) * 1973-06-25 1977-07-26 Kefalas A/S Compositions of and method of treating with the alpha-isomer of 2-chloro-9-[3'-(N'-2-hydroxyethylpiperazino-N)-propylidene]-thiaxanthene, carboxylic acid esters thereof and acid addition salts of these compounds
GB1469108A (en) * 1973-06-25 1977-03-30 Kefalas As Thiaxanthene derivative
NZ196284A (en) * 1980-02-29 1983-12-16 Kefalas As 1-piperazino-3-phenylindane derivatives:pharmaceutical compositions
IE55972B1 (en) * 1982-10-07 1991-03-13 Kefalas As Phenylindene derivatives,acid addition salts thereof,and methods of preparation
HU198036B (en) * 1983-08-22 1989-07-28 Hoechst Roussel Pharma Process for production of derivatives of 3-piperidil-/1h/-indasole and medical preparatives containing them
GB8427125D0 (en) * 1984-10-26 1984-12-05 Lundbeck & Co As H Organic compounds
WO1986003601A1 (en) * 1984-12-03 1986-06-19 Hughes Aircraft Company Variable lens and birefringence compensator for continuous operation
IE58370B1 (en) * 1985-04-10 1993-09-08 Lundbeck & Co As H Indole derivatives
DE3521761A1 (de) * 1985-06-19 1987-01-02 Bayer Ag Neue 1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln
GB8628644D0 (en) * 1986-12-01 1987-01-07 Lunbeck A S H Intermediates
GB8704572D0 (en) * 1987-02-26 1987-04-01 Lundbeck & Co As H Organic compounds
MX173362B (es) * 1987-03-02 1994-02-23 Pfizer Compuestos de piperazinil heterociclicos y procedimiento para su preparacion
EP0302423A3 (en) * 1987-08-07 1991-01-09 Hoechst-Roussel Pharmaceuticals Incorporated 1-phenyl-3-(1-piperazinyl)-1h-indazoles, a process and intermediates for their preparation, and the use thereof as medicaments
US4831031A (en) * 1988-01-22 1989-05-16 Pfizer Inc. Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity
GB8830312D0 (en) * 1988-12-28 1989-02-22 Lundbeck & Co As H Heterocyclic compounds
EP0507863A4 (en) * 1989-12-28 1993-07-07 Virginia Commonwealth University Sigma receptor ligands and the use thereof
DK152090D0 (da) * 1990-06-22 1990-06-22 Lundbaek A S H Piperidylsubstituerede indolderivater
DK158590D0 (da) * 1990-07-02 1990-07-02 Lundbeck & Co As H Indolderivater
DK286990D0 (da) * 1990-12-04 1990-12-04 Lundbeck & Co As H Indanderivater
US5643784A (en) * 1990-12-04 1997-07-01 H, Lundbeck A/S Indan derivatives

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FI945042A (sv) 1994-10-26
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NO306946B1 (no) 2000-01-17
RU2114106C1 (ru) 1998-06-27
PT638073E (pt) 2000-11-30
AU4059993A (en) 1993-11-29
CL2003002050A1 (es) 2005-01-07
ES2148227T3 (es) 2000-10-16
CZ261994A3 (en) 1995-05-17
WO1993022293A1 (en) 1993-11-11
CZ281676B6 (cs) 1996-12-11
KR100267635B1 (ko) 2000-11-01
DE69328901T2 (de) 2001-01-11
IL105464A (en) 1998-01-04
ATE194003T1 (de) 2000-07-15
HU9403098D0 (en) 1994-12-28
IL105464A0 (en) 1993-08-18
CA2134566A1 (en) 1993-11-11
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DK0638073T3 (da) 2000-11-06
DE69328901D1 (de) 2000-07-27
GR3034396T3 (en) 2000-12-29
AU669709B2 (en) 1996-06-20
NO944090L (no) 1994-12-20
RU94045948A (ru) 1996-09-10
KR950701323A (ko) 1995-03-23
HU211909A9 (en) 1996-01-29
ZA932840B (en) 1993-11-23
US5807855A (en) 1998-09-15
HK1013816A1 (en) 1999-09-10
NO944090D0 (no) 1994-10-27
DK55192D0 (da) 1992-04-28
SK129394A3 (en) 1995-05-10
JP3255416B2 (ja) 2002-02-12
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NZ252098A (en) 1996-05-28
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