NO318936B1 - (4-piperidinyl)-1H-2benzopyranderivater som er anvendbare som antipsykotiske midler, farmasoytisk preparat inneholdende derivatene samt fremgangsmate for fremstilling derav. - Google Patents

(4-piperidinyl)-1H-2benzopyranderivater som er anvendbare som antipsykotiske midler, farmasoytisk preparat inneholdende derivatene samt fremgangsmate for fremstilling derav. Download PDF

Info

Publication number: NO318936B1
Authority: NO; Norway
Prior art keywords: fluorophenyl; pyridinyl; phenylpropyl; imidazole; compound
Prior art date: 1997-02-07

Application number

NO19993812A

Other languages

English (en)

Norwegian (no)

Other versions

NO993812D0 (no

NO993812L (no

Inventor

Joseph Thomas Strupczewski

Kenneth J Bordeau

Shelley L Pavlek

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.)

1997-02-07

Filing date

1999-08-06

Publication date

2005-05-30

1999-08-06 Application filed by Aventis Pharma Inc filed Critical Aventis Pharma Inc

1999-08-06 Publication of NO993812D0 publication Critical patent/NO993812D0/no

1999-10-05 Publication of NO993812L publication Critical patent/NO993812L/no

2005-05-30 Publication of NO318936B1 publication Critical patent/NO318936B1/no

Links

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BGQDJILSOPGZQP-UHFFFAOYSA-N 4-(1h-isochromen-1-yl)piperidine Chemical class C1CNCCC1C1C2=CC=CC=C2C=CO1 BGQDJILSOPGZQP-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 86
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 14
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 14
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125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims 2
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HDFYEYJOYNGSFP-UHFFFAOYSA-N 4-[2-(3-cyclopentylprop-1-ynyl)-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(C#CCC2CCCC2)=N1 HDFYEYJOYNGSFP-UHFFFAOYSA-N 0.000 claims 1
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XOJLNOCCMFAJPV-UHFFFAOYSA-N 4-[2-(5-butylsulfonylpent-1-ynyl)-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCS(=O)(=O)CCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 XOJLNOCCMFAJPV-UHFFFAOYSA-N 0.000 claims 1
IOKBLNMQALUDJY-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-(5-phenylpent-1-ynyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(C#CCCCC=2C=CC=CC=2)=N1 IOKBLNMQALUDJY-UHFFFAOYSA-N 0.000 claims 1
IMWNIKIDZJRIGK-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-iodo-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(I)=N1 IMWNIKIDZJRIGK-UHFFFAOYSA-N 0.000 claims 1
CBHBNYVEBBXTJR-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-oct-1-ynyl-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 CBHBNYVEBBXTJR-UHFFFAOYSA-N 0.000 claims 1
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239000003586 protic polar solvent Substances 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
210000002637 putamen Anatomy 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007790 scraping Methods 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000015883 synaptic transmission, dopaminergic Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/453—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems

Landscapes

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

NO19993812A 1997-02-07 1999-08-06 (4-piperidinyl)-1H-2benzopyranderivater som er anvendbare som antipsykotiske midler, farmasoytisk preparat inneholdende derivatene samt fremgangsmate for fremstilling derav. NO318936B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US79710797A	1997-02-07	1997-02-07
PCT/US1998/000979 WO1998034933A1 (fr)	1997-02-07	1998-01-20	Derives de (4-piperidinyl)-1h-2-benzopyrane convenant comme antipsychotiques

Publications (3)

Publication Number	Publication Date
NO993812D0 NO993812D0 (no)	1999-08-06
NO993812L NO993812L (no)	1999-10-05
NO318936B1 true NO318936B1 (no)	2005-05-30

Family

ID=25169927

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19993812A NO318936B1 (no)	1997-02-07	1999-08-06	(4-piperidinyl)-1H-2benzopyranderivater som er anvendbare som antipsykotiske midler, farmasoytisk preparat inneholdende derivatene samt fremgangsmate for fremstilling derav.

Country Status (21)

Country	Link
EP (1)	EP1015446B1 (fr)
JP (1)	JP4177461B2 (fr)
KR (1)	KR100509878B1 (fr)
CN (1)	CN1092653C (fr)
AR (1)	AR011614A1 (fr)
AT (1)	ATE236150T1 (fr)
AU (1)	AU725301B2 (fr)
BR (1)	BRPI9807312B8 (fr)
CA (1)	CA2281702C (fr)
CY (1)	CY2324B1 (fr)
DE (1)	DE69812980T2 (fr)
DK (1)	DK1015446T3 (fr)
ES (1)	ES2194303T3 (fr)
HU (1)	HUP0001308A3 (fr)
IL (1)	IL131243A (fr)
NO (1)	NO318936B1 (fr)
NZ (1)	NZ336719A (fr)
PT (1)	PT1015446E (fr)
TW (1)	TW518333B (fr)
WO (1)	WO1998034933A1 (fr)
ZA (1)	ZA98831B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE459618T1 (de) *	2004-04-29	2010-03-15	Aventis Pharma Inc	3-piperidinylisochroman-5-ole als dopaminagonisten
EP1748767B1 (fr)	2004-05-28	2011-12-28	Unigen, Inc.	1-(3-methyl-2,4-dimethoxyphenyl)-3-(2',4'-dihydroxyphenyl)-propane comme inhibiteur puissant de la tyrosinase
AU2008280187B2 (en)	2007-07-26	2013-05-16	F. Hoffmann-La Roche Ag	Dual modulators of 5-HT2A and D3 receptors
KR101988329B1 (ko)	2008-07-21	2019-06-12	유니젠, 인크.	일련의 피부-화이트닝(라이트닝) 화합물
US8877778B2 (en)	2010-12-15	2014-11-04	Hoffmann-La Roche Inc.	Benzofurane compounds
CN102079720B (zh) *	2011-01-20	2013-02-06	蚌埠丰原医药科技发展有限公司	一种制备1-苄基-4-哌啶甲醛的方法
JP6216312B2 (ja)	2011-03-24	2017-10-18	ユニゲン・インコーポレーテッド	ジアリールプロパンを調製するための化合物及び方法
US8921397B2 (en)	2011-05-04	2014-12-30	Hoffmann-La Roche Inc.	Benzofurane-piperidine compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1552004A (en) *	1976-05-26	1979-09-05	Takeda Chemical Industries Ltd	Isochroman derivatives
US4963568A (en) *	1989-05-31	1990-10-16	Abbott Laboratories	Dopamine agonists

1998
- 1998-01-20 CA CA002281702A patent/CA2281702C/fr not_active Expired - Lifetime
- 1998-01-20 AT AT98902628T patent/ATE236150T1/de active
- 1998-01-20 HU HU0001308A patent/HUP0001308A3/hu unknown
- 1998-01-20 IL IL13124398A patent/IL131243A/en not_active IP Right Cessation
- 1998-01-20 DK DK98902628T patent/DK1015446T3/da active
- 1998-01-20 CN CN98802357A patent/CN1092653C/zh not_active Expired - Lifetime
- 1998-01-20 NZ NZ336719A patent/NZ336719A/xx unknown
- 1998-01-20 EP EP98902628A patent/EP1015446B1/fr not_active Expired - Lifetime
- 1998-01-20 BR BRPI9807312A patent/BRPI9807312B8/pt not_active IP Right Cessation
- 1998-01-20 AU AU59237/98A patent/AU725301B2/en not_active Expired
- 1998-01-20 WO PCT/US1998/000979 patent/WO1998034933A1/fr not_active Ceased
- 1998-01-20 ES ES98902628T patent/ES2194303T3/es not_active Expired - Lifetime
- 1998-01-20 DE DE69812980T patent/DE69812980T2/de not_active Expired - Lifetime
- 1998-01-20 PT PT98902628T patent/PT1015446E/pt unknown
- 1998-01-20 JP JP53461798A patent/JP4177461B2/ja not_active Expired - Fee Related
- 1998-01-20 KR KR10-1999-7007127A patent/KR100509878B1/ko not_active Expired - Fee Related
- 1998-02-02 ZA ZA98831A patent/ZA98831B/xx unknown
- 1998-02-03 TW TW087101327A patent/TW518333B/zh not_active IP Right Cessation
- 1998-02-03 AR ARP980100456A patent/AR011614A1/es active IP Right Grant
1999
- 1999-08-06 NO NO19993812A patent/NO318936B1/no unknown
2003
- 2003-04-30 CY CY0300037A patent/CY2324B1/xx unknown

Also Published As

Publication number	Publication date
AU5923798A (en)	1998-08-26
HUP0001308A2 (hu)	2001-06-28
PT1015446E (pt)	2003-08-29
KR100509878B1 (ko)	2005-08-25
ES2194303T3 (es)	2003-11-16
NZ336719A (en)	2000-10-27
EP1015446B1 (fr)	2003-04-02
CA2281702A1 (fr)	1998-08-13
ATE236150T1 (de)	2003-04-15
DK1015446T3 (da)	2003-07-14
CY2324B1 (en)	2003-11-14
HUP0001308A3 (en)	2001-07-30
KR20000070862A (ko)	2000-11-25
IL131243A (en)	2004-02-19
DE69812980D1 (de)	2003-05-08
ZA98831B (en)	1998-08-07
BR9807312B1 (pt)	2013-10-29
WO1998034933A1 (fr)	1998-08-13
EP1015446A1 (fr)	2000-07-05
BRPI9807312B8 (pt)	2016-09-13
CN1092653C (zh)	2002-10-16
JP4177461B2 (ja)	2008-11-05
NO993812D0 (no)	1999-08-06
TW518333B (en)	2003-01-21
DE69812980T2 (de)	2003-11-13
CN1246859A (zh)	2000-03-08
IL131243A0 (en)	2001-01-28
AU725301B2 (en)	2000-10-12
NO993812L (no)	1999-10-05
CA2281702C (fr)	2006-04-11
AR011614A1 (es)	2000-08-30
HK1027812A1 (en)	2001-01-23
JP2001512436A (ja)	2001-08-21
BR9807312A (pt)	2000-05-02

Publication	Publication Date	Title
US5100902A (en)	1992-03-31	1,2-benzisoxazole compounds
KR100815772B1 (ko)	2008-03-20	신규 고리상 아미드 유도체
MXPA05003674A (es)	2005-06-08	Compuesto de 2,3-dihidro-6-nitroimidazo[2,1-b]oxazol.
WO1994007890A1 (fr)	1994-04-14	Compose pyrimidine
TW200908961A (en)	2009-03-01	New pharmaceutical compounds
MXPA02000978A (es)	2002-08-12	Antagonistas del receptor de quimioquina y metodosde uso de los mismos.
JP5936669B2 (ja)	2016-06-22	ケモカイン受容体アンタゴニストおよびその使用方法
CA2240964C (fr)	2002-06-25	Piperidones, antagonistes de la tachykinine
WO2009081259A1 (fr)	2009-07-02	Dérivés phénoxy-pyridylés
EP1015446B1 (fr)	2003-04-02	Derives de (4-piperidinyl)-1h-2-benzopyrane convenant comme antipsychotiques
JPWO2003095427A1 (ja)	2005-09-15	スピロ環化合物
NO177534B (no)	1995-06-26	Analogifremgangsmåte for fremstilling av terapeutisk aktive tricykliske aminer
US9663537B2 (en)	2017-05-30	Chemokine receptor antagonists and methods of use
US6004982A (en)	1999-12-21	4-piperidinyl) H-2-benzopyran derivatives useful as antipsychotic agents
US20050070549A1 (en)	2005-03-31	Chemokine receptor antagonists and methods of use thereof
US3476761A (en)	1969-11-04	10- and 11-(4-piperidyl)dibenzo (a,d)cycloheptatrienes
EP0102034B1 (fr)	1988-04-20	Composés de la spiro(2H-1,4-benzodioxépine-3(5H)4'-pipéridine et 3'-pyrrolidino), procédé pour leur préparation et leur utilisation comme médicaments
MXPA99007307A (es)	2000-01-01	Derivados de (4-piperidinil)-1h-2-benzopirano utiles como agentes antipsicoticos
IL26424A (en)	1970-08-19	10-or 11-piperidyl-dibenzo(a,d)cycloheptadiene derivatives and their preparation
HK1027812B (en)	2003-12-12	(4 - piperidinyl)-1h - 2 - benzopyran derivatives useful as antipsychotic agents