UA77526C2 - Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy - Google Patents

Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy Download PDF

Info

Publication number: UA77526C2
Authority: UA; Ukraine
Prior art keywords: formula; compound; methyl; trifluoromethyl; phenyl
Prior art date: 2002-06-07

Application number

UA20041210010A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Sanofi Aventis

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.)

2002-06-07

Filing date

2003-05-06

Publication date

2006-12-15

2003-05-06 Application filed by Sanofi Aventis filed Critical Sanofi Aventis

2006-12-15 Publication of UA77526C2 publication Critical patent/UA77526C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 66
238000002360 preparation method Methods 0.000 title claims description 150
238000002560 therapeutic procedure Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 423
-1 trifluoromethoxy radical Chemical class 0.000 claims abstract description 117
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 27
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
125000005843 halogen group Chemical group 0.000 claims abstract description 22
229910052799 carbon Inorganic materials 0.000 claims abstract description 21
125000003118 aryl group Chemical group 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
125000000217 alkyl group Chemical group 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
150000003839 salts Chemical group 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 22
239000012453 solvate Substances 0.000 claims description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 10
229910052700 potassium Inorganic materials 0.000 claims description 10
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 10
150000001412 amines Chemical group 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 7
230000006378 damage Effects 0.000 claims description 7
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 6
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
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230000006870 function Effects 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 4
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
208000027418 Wounds and injury Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
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125000004093 cyano group Chemical group *C#N 0.000 claims description 3
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125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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208000023275 Autoimmune disease Diseases 0.000 claims description 2
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206010027476 Metastases Diseases 0.000 claims description 2
208000031481 Pathologic Constriction Diseases 0.000 claims description 2
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230000001684 chronic effect Effects 0.000 claims description 2
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230000036262 stenosis Effects 0.000 claims description 2
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229940079593 drug Drugs 0.000 claims 2
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
230000003676 hair loss Effects 0.000 claims 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
230000001225 therapeutic effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
239000000203 mixture Substances 0.000 description 163
239000000047 product Substances 0.000 description 141
239000002904 solvent Substances 0.000 description 111
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
238000003756 stirring Methods 0.000 description 78
239000012074 organic phase Substances 0.000 description 73
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
239000003480 eluent Substances 0.000 description 42
239000000741 silica gel Substances 0.000 description 42
229910002027 silica gel Inorganic materials 0.000 description 42
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 39
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WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000000706 filtrate Substances 0.000 description 29
239000003054 catalyst Substances 0.000 description 28
239000012047 saturated solution Substances 0.000 description 27
239000011734 sodium Substances 0.000 description 26
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 22
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 22
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
239000002244 precipitate Substances 0.000 description 22
238000010992 reflux Methods 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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238000001819 mass spectrum Methods 0.000 description 15
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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- 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
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UA20041210010A 2002-06-07 2003-05-06 Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy UA77526C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0207001		2002-06-07
PCT/FR2003/001685 WO2003104225A1 (fr)	2002-06-07	2003-06-05	Derives de piperazinylacylpiperidine, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
UA77526C2 true UA77526C2 (en)	2006-12-15

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ID=29724874

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Application Number	Title	Priority Date	Filing Date
UA20041210010A UA77526C2 (en)	2002-06-07	2003-05-06	Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy

Country Status (29)

Country	Link
US (2)	US7294628B2 (sr)
EP (2)	EP1513836B1 (sr)
JP (2)	JP4441401B2 (sr)
KR (1)	KR100970812B1 (sr)
CN (1)	CN100448875C (sr)
AR (2)	AR040247A1 (sr)
AT (2)	ATE325122T1 (sr)
AU (2)	AU2003255645A1 (sr)
BR (1)	BR0311828A (sr)
CA (1)	CA2487840C (sr)
CY (2)	CY1107330T1 (sr)
DE (2)	DE60307632T2 (sr)
DK (2)	DK1513836T3 (sr)
EA (1)	EA007501B1 (sr)
ES (2)	ES2264001T3 (sr)
HR (1)	HRP20041157B1 (sr)
IS (1)	IS2302B (sr)
MA (1)	MA27233A1 (sr)
ME (1)	MEP11508A (sr)
MX (1)	MXPA04012341A (sr)
NO (1)	NO329669B1 (sr)
NZ (1)	NZ537044A (sr)
PL (1)	PL208711B1 (sr)
PT (2)	PT1513835E (sr)
RS (2)	RS52588B (sr)
TW (2)	TWI319400B (sr)
UA (1)	UA77526C2 (sr)
WO (2)	WO2003104226A1 (sr)
ZA (1)	ZA200409823B (sr)

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FR2862968B1 (fr) *	2003-12-01	2006-08-04	Sanofi Synthelabo	Derives de 4-[(arylmethyl)aminomethyl]piperidine, leur preparation et leur application en therapeutique
FR2862967B1 (fr) *	2003-12-01	2006-08-04	Sanofi Synthelabo	Derives de (4-phenylpiperazin-1-yl)acylpiperidine, leur preparation et leur application en therapeutique
EP1706392A2 (en) *	2004-01-08	2006-10-04	Syngenta Participations AG	Pesticidal heterocyclic dihaloallyl compounds
WO2006008259A1 (en) *	2004-07-16	2006-01-26	Janssen Pharmaceutica N.V.	Dimeric compounds of piperidine, piperazine or morpholine or their 7-membered analogs suitabale for the treatment of neurodegenerative disorders
EP2289510A1 (en) *	2004-09-20	2011-03-02	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes
WO2006113097A2 (en)	2005-04-15	2006-10-26	The University Of North Carolina At Chapel Hill	Methods of facilitating cell survival using neurotrophin mimetics
JP5147866B2 (ja) *	2007-03-15	2013-02-20	メルク・シャープ・アンド・ドーム・コーポレーション	グルカン合成酵素阻害剤として有用であるピリダジノン誘導体
DE102007026341A1 (de)	2007-06-06	2008-12-11	Merck Patent Gmbh	Benzoxazolonderivate
DE102007032507A1 (de)	2007-07-12	2009-04-02	Merck Patent Gmbh	Pyridazinonderivate
FR2932482B1 (fr) *	2008-06-13	2010-10-08	Sanofi Aventis	Nouveaux derives de (phenyl-3,6-dihydro-2h-pyridinyl)- (piperazinyl ponte)-1-alcanone et leur utilisation comme inhibiteurs de p75
FR2932481B1 (fr) *	2008-06-13	2010-10-08	Sanofi Aventis	Derives de 4-{2-°4-phenyl-3,6-dihydro-2h-pyridin-1-yl!-2- oxo-alkyl}-1-piperazin-2-one, leur preparation et leur application en therapeutique.
WO2011060262A1 (en)	2009-11-12	2011-05-19	Pharmatrophix, Inc.	Crystalline forms of neurotrophin mimetic compounds and their salts
US10273219B2 (en)	2009-11-12	2019-04-30	Pharmatrophix, Inc.	Crystalline forms of neurotrophin mimetic compounds and their salts
AU2010333338A1 (en)	2009-12-14	2012-08-02	Merck Patent Gmbh	Sphingosine kinase inhibitors
FR2953839A1 (fr) *	2009-12-14	2011-06-17	Sanofi Aventis	Nouveaux derives d'(heterocycle-piperidine condensee)-(piperazinyl)-1alcanone ou d'(heterocycle-pyrrolidine condensee)-(piperazinyl)-1alcanone et leur utilisation comme inhibiteurs de p75
FR2953836B1 (fr)	2009-12-14	2012-03-16	Sanofi Aventis	Nouveaux derives (heterocycle-tetrahydro-pyridine)-(piperazinyl)-1-alcanone et (heterocycle-dihydro-pyrrolidine)-(piperazinyl)-1-alcanone et leur utilisation comme inhibiteurs de p75
EP2606894A1 (en)	2011-12-20	2013-06-26	Sanofi	Novel therapeutic use of p75 receptor antagonists
US12435078B2 (en)	2017-09-18	2025-10-07	Gfb (Abc), Llc	Pyridazinones and methods of use thereof
LT3852533T (lt)	2018-09-18	2024-06-10	Gfb (Abc), Llc	Piridazinonai ir jų naudojimo būdai
CA3136632A1 (en)	2019-04-11	2020-10-15	Goldfinch Bio, Inc.	Spray-dried formulation of a pyridazinone trpc5 inhibitor
EP3858439A1 (en) *	2020-02-03	2021-08-04	Esteve Pharmaceuticals, S.A.	Amide derivatives having multimodal activity against pain

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US4994455A (en) *	1987-10-26	1991-02-19	Pfizer Inc.	Anti-anxiety agents
FR2747041B1 (fr) *	1996-04-05	1998-05-22	Cird Galderma	Utilisation de derives benzonaphtaleniques pour la fabrication de medicaments destines au traitement des neuropathies
US6468990B1 (en)	1999-05-17	2002-10-22	Queen's University At Kingston	Method of inhibiting binding of nerve growth factor to p75 NTR receptor
FR2803593B1 (fr)	2000-01-06	2002-02-15	Sanofi Synthelabo	Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant

2003
- 2003-05-06 UA UA20041210010A patent/UA77526C2/uk unknown
- 2003-06-05 DE DE60307632T patent/DE60307632T2/de not_active Expired - Lifetime
- 2003-06-05 BR BR0311828-2A patent/BR0311828A/pt not_active IP Right Cessation
- 2003-06-05 NZ NZ537044A patent/NZ537044A/en not_active IP Right Cessation
- 2003-06-05 ME MEP-115/08A patent/MEP11508A/xx unknown
- 2003-06-05 ES ES03757109T patent/ES2264001T3/es not_active Expired - Lifetime
- 2003-06-05 DK DK03757109T patent/DK1513836T3/da active
- 2003-06-05 JP JP2004511296A patent/JP4441401B2/ja not_active Expired - Fee Related
- 2003-06-05 KR KR1020047019860A patent/KR100970812B1/ko not_active Expired - Fee Related
- 2003-06-05 ES ES03757108T patent/ES2271637T3/es not_active Expired - Lifetime
- 2003-06-05 MX MXPA04012341A patent/MXPA04012341A/es active IP Right Grant
- 2003-06-05 AU AU2003255645A patent/AU2003255645A1/en not_active Abandoned
- 2003-06-05 CA CA2487840A patent/CA2487840C/en not_active Expired - Fee Related
- 2003-06-05 EA EA200401470A patent/EA007501B1/ru not_active IP Right Cessation
- 2003-06-05 HR HR20041157 patent/HRP20041157B1/xx not_active IP Right Cessation
- 2003-06-05 PT PT03757108T patent/PT1513835E/pt unknown
- 2003-06-05 AU AU2003255644A patent/AU2003255644B2/en not_active Ceased
- 2003-06-05 CN CNB038188082A patent/CN100448875C/zh not_active Expired - Fee Related
- 2003-06-05 WO PCT/FR2003/001686 patent/WO2003104226A1/fr not_active Ceased
- 2003-06-05 DK DK03757108T patent/DK1513835T3/da active
- 2003-06-05 PT PT03757109T patent/PT1513836E/pt unknown
- 2003-06-05 US US10/516,808 patent/US7294628B2/en not_active Expired - Lifetime
- 2003-06-05 PL PL374729A patent/PL208711B1/pl not_active IP Right Cessation
- 2003-06-05 JP JP2004511295A patent/JP4437075B2/ja not_active Expired - Fee Related
- 2003-06-05 US US10/516,704 patent/US7468368B2/en not_active Expired - Lifetime
- 2003-06-05 AT AT03757109T patent/ATE325122T1/de active
- 2003-06-05 WO PCT/FR2003/001685 patent/WO2003104225A1/fr not_active Ceased
- 2003-06-05 RS RS20050014A patent/RS52588B/sr unknown
- 2003-06-05 EP EP03757109A patent/EP1513836B1/fr not_active Expired - Lifetime
- 2003-06-05 DE DE60305037T patent/DE60305037T2/de not_active Expired - Lifetime
- 2003-06-05 RS YUP-2005/0014A patent/RS20050014A/sr unknown
- 2003-06-05 EP EP03757108A patent/EP1513835B1/fr not_active Expired - Lifetime
- 2003-06-05 AT AT03757108T patent/ATE336491T1/de active
- 2003-06-06 TW TW092115443A patent/TWI319400B/zh not_active IP Right Cessation
- 2003-06-06 AR ARP030102018A patent/AR040247A1/es active IP Right Grant
- 2003-06-06 TW TW092115416A patent/TWI283671B/zh not_active IP Right Cessation
- 2003-06-06 AR ARP030102017A patent/AR040246A1/es active IP Right Grant
2004
- 2004-12-02 IS IS7579A patent/IS2302B/is unknown
- 2004-12-03 ZA ZA200409823A patent/ZA200409823B/en unknown
- 2004-12-03 MA MA27980A patent/MA27233A1/fr unknown
- 2004-12-06 NO NO20045331A patent/NO329669B1/no not_active IP Right Cessation
2006
- 2006-08-03 CY CY20061101094T patent/CY1107330T1/el unknown
- 2006-11-15 CY CY20061101660T patent/CY1105784T1/el unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2497819C2 (ru) *	2007-05-21	2013-11-10	Ривайва Фармасьютикалс, Инк.	Композиции, синтез и способы применения атипичных нейролептиков на основе хинолина

Also Published As

Publication number	Publication date
TW200400185A (en)	2004-01-01
RS52588B (sr)	2013-04-30
PL208711B1 (pl)	2011-05-31
EA200401470A1 (ru)	2005-06-30
CA2487840C (en)	2011-05-17
HRP20041157A2 (en)	2005-06-30
AU2003255644B2 (en)	2009-02-05
CY1107330T1 (el)	2012-11-21
RS20050014A (sr)	2007-06-04
KR20050008802A (ko)	2005-01-21
ATE336491T1 (de)	2006-09-15
DK1513835T3 (da)	2006-12-27
WO2003104226A1 (fr)	2003-12-18
MEP11508A (en)	2010-06-10
US20050176722A1 (en)	2005-08-11
CN1675203A (zh)	2005-09-28
HRP20041157B1 (en)	2012-11-30
US7294628B2 (en)	2007-11-13
AR040247A1 (es)	2005-03-23
CY1105784T1 (el)	2011-02-02
EP1513836A1 (fr)	2005-03-16
PL374729A1 (en)	2005-10-31
DK1513836T3 (da)	2006-09-11
ZA200409823B (en)	2006-07-26
EA007501B1 (ru)	2006-10-27
JP2005533051A (ja)	2005-11-04
AU2003255644A1 (en)	2003-12-22
AR040246A1 (es)	2005-03-23
JP2005534661A (ja)	2005-11-17
DE60307632D1 (de)	2006-09-28
DE60305037T2 (de)	2006-12-14
PT1513835E (pt)	2006-12-29
BR0311828A (pt)	2005-03-29
US20060167007A1 (en)	2006-07-27
NO329669B1 (no)	2010-11-29
ES2264001T3 (es)	2006-12-16
EP1513835B1 (fr)	2006-08-16
TWI319400B (en)	2010-01-11
TWI283671B (en)	2007-07-11
EP1513835A1 (fr)	2005-03-16
TW200407321A (en)	2004-05-16
EP1513836B1 (fr)	2006-05-03
DE60305037D1 (de)	2006-06-08
WO2003104225A1 (fr)	2003-12-18
US7468368B2 (en)	2008-12-23
HK1076110A1 (zh)	2006-01-06
NO20045331L (no)	2005-03-07
PT1513836E (pt)	2006-09-29
IS2302B (is)	2007-10-15
CN100448875C (zh)	2009-01-07
KR100970812B1 (ko)	2010-07-16
IS7579A (is)	2004-12-02
JP4437075B2 (ja)	2010-03-24
DE60307632T2 (de)	2007-08-09
ATE325122T1 (de)	2006-06-15
AU2003255645A1 (en)	2003-12-22
MXPA04012341A (es)	2005-09-30
CA2487840A1 (en)	2003-12-18
MA27233A1 (fr)	2005-02-01
NZ537044A (en)	2006-08-31
JP4441401B2 (ja)	2010-03-31
ES2271637T3 (es)	2007-04-16

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UA77526C2 - Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy - Google Patents

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ID=29724874

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Country Status (29)

Cited By (1)

Families Citing this family (21)

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