UA80555C2 - Acutumine and acutumine compounds, synthesis and use - Google Patents

Acutumine and acutumine compounds, synthesis and use Download PDF

Info

Publication number: UA80555C2
Authority: UA; Ukraine
Prior art keywords: formula; spiro; hexahydro; inden; compounds
Prior art date: 2002-06-25

Application number

UAA200500667A

Other languages

English (en)

Ukrainian (uk)

Inventor

Pierre Lieustage

Daniel-Henry Keniard

Pierre Renard

Original Assignee

Servier Lab

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.)

2002-06-25

Filing date

2003-06-16

Publication date

2007-10-10

2003-06-16 Application filed by Servier Lab filed Critical Servier Lab

2007-10-10 Publication of UA80555C2 publication Critical patent/UA80555C2/uk

Links

FSXRARBVZZKCGJ-FMAJMWNWSA-N Acutumine Chemical compound O[C@@H]1C(OC)=CC(=O)[C@@]11[C@@]2(CC(=O)C(OC)=C3OC)CCN(C)[C@@]23C[C@@H]1Cl FSXRARBVZZKCGJ-FMAJMWNWSA-N 0.000 title abstract 3
QHDJUCISALFSTI-XXLQSDOLSA-N acutumine Natural products CO[C@@H]1C(OC)=CC(=O)[C@@]11[C@@]2(CC(=O)C(OC)=C3OC)CCN(C)[C@@]23C[C@@H]1Cl QHDJUCISALFSTI-XXLQSDOLSA-N 0.000 title abstract 2
FSXRARBVZZKCGJ-UHFFFAOYSA-N dauricumine Natural products OC1C(OC)=CC(=O)C11C2(CC(=O)C(OC)=C3OC)CCN(C)C23CC1Cl FSXRARBVZZKCGJ-UHFFFAOYSA-N 0.000 title abstract 2
230000015572 biosynthetic process Effects 0.000 title description 2
238000003786 synthesis reaction Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 130
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
229910052801 chlorine Chemical group 0.000 claims abstract description 6
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
125000003003 spiro group Chemical group 0.000 claims description 77
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 20
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
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SBALNGLYQFMKPR-NQTWQHAWSA-N Acutumidine Chemical compound O[C@@H]1C(OC)=CC(=O)[C@@]11[C@@]2(CC(=O)C(OC)=C3OC)CCN[C@@]23C[C@@H]1Cl SBALNGLYQFMKPR-NQTWQHAWSA-N 0.000 claims description 6
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SBALNGLYQFMKPR-UHFFFAOYSA-N dauricumidine Natural products OC1C(OC)=CC(=O)C11C2(CC(=O)C(OC)=C3OC)CCNC23CC1Cl SBALNGLYQFMKPR-UHFFFAOYSA-N 0.000 claims description 6
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229960004526 piracetam Drugs 0.000 description 1
229960003389 pramiracetam Drugs 0.000 description 1
ZULJGOSFKWFVRX-UHFFFAOYSA-N pramiracetam Chemical compound CC(C)N(C(C)C)CCNC(=O)CN1CCCC1=O ZULJGOSFKWFVRX-UHFFFAOYSA-N 0.000 description 1
OGJKMZVUJJYWKO-UHFFFAOYSA-N proaporphine Natural products C1=2C3=C(OC)C(OC)=CC=2CCNC1CC13C=CC(=O)C=C1 OGJKMZVUJJYWKO-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229960001685 tacrine Drugs 0.000 description 1
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- 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
- A61P25/14—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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Indole Compounds (AREA)

UAA200500667A 2002-06-25 2003-06-16 Acutumine and acutumine compounds, synthesis and use UA80555C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CNA021214794A CN1465566A (zh)	2002-06-25	2002-06-25	青防己碱与青防己碱化合物、合成和用途
PCT/IB2003/002600 WO2004000815A1 (fr)	2002-06-25	2003-06-16	Acutumine et composes de l'acutumine, leur synthese et leur utilisation

Publications (1)

Publication Number	Publication Date
UA80555C2 true UA80555C2 (en)	2007-10-10

Family

ID=29742994

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200500667A UA80555C2 (en)	2002-06-25	2003-06-16	Acutumine and acutumine compounds, synthesis and use

Country Status (19)

Country	Link
US (1)	US20060167076A1 (fr)
EP (1)	EP1608625A1 (fr)
JP (1)	JP2006501174A (fr)
KR (1)	KR100677018B1 (fr)
CN (2)	CN1465566A (fr)
AR (1)	AR040462A1 (fr)
AU (1)	AU2003242278A1 (fr)
BR (1)	BR0312444A (fr)
CA (1)	CA2491214A1 (fr)
EA (1)	EA007229B1 (fr)
GE (1)	GEP20074178B (fr)
MA (1)	MA27264A1 (fr)
MX (1)	MXPA05000076A (fr)
NO (1)	NO20050214L (fr)
NZ (1)	NZ537405A (fr)
PL (1)	PL374039A1 (fr)
UA (1)	UA80555C2 (fr)
WO (1)	WO2004000815A1 (fr)
ZA (1)	ZA200410280B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011030798A1 (fr) *	2009-09-09	2011-03-17	大日本住友製薬株式会社	Dérivés de 8-oxodihydropurine
AU2014101153A4 (en) *	2014-01-03	2014-10-23	Macau University Of Science And Technology	A Group of Alkaloids, the Novel Autophagic Enhancers for Treatment of Cancers and Neurodegenerative Conditions Thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3479423D1 (en) *	1984-02-29	1989-09-21	Covex Sa	Citrate of vinpocetine, and process for its preparation
CN1052225A (zh) *	1990-02-07	1991-06-12	福建省仙游电机厂	一种大比功的汽车发电机及其制造方法
CN1101812C (zh) *	1997-12-19	2003-02-19	中国科学院上海药物研究所	石菖蒲中菖蒲碱及它们的用途

2002
- 2002-06-25 CN CNA021214794A patent/CN1465566A/zh active Pending
2003
- 2003-06-16 NZ NZ537405A patent/NZ537405A/xx unknown
- 2003-06-16 GE GEAP8597A patent/GEP20074178B/en unknown
- 2003-06-16 JP JP2004515147A patent/JP2006501174A/ja active Pending
- 2003-06-16 MX MXPA05000076A patent/MXPA05000076A/es not_active Application Discontinuation
- 2003-06-16 US US10/519,418 patent/US20060167076A1/en not_active Abandoned
- 2003-06-16 AU AU2003242278A patent/AU2003242278A1/en not_active Abandoned
- 2003-06-16 CA CA002491214A patent/CA2491214A1/fr not_active Abandoned
- 2003-06-16 UA UAA200500667A patent/UA80555C2/uk unknown
- 2003-06-16 PL PL03374039A patent/PL374039A1/xx not_active Application Discontinuation
- 2003-06-16 CN CNB038191261A patent/CN1303069C/zh not_active Expired - Fee Related
- 2003-06-16 EA EA200500081A patent/EA007229B1/ru not_active IP Right Cessation
- 2003-06-16 WO PCT/IB2003/002600 patent/WO2004000815A1/fr not_active Ceased
- 2003-06-16 BR BR0312444-4A patent/BR0312444A/pt not_active IP Right Cessation
- 2003-06-16 KR KR1020047021154A patent/KR100677018B1/ko not_active Expired - Fee Related
- 2003-06-16 EP EP03732907A patent/EP1608625A1/fr not_active Withdrawn
- 2003-06-23 AR AR20030102234A patent/AR040462A1/es unknown
2004
- 2004-12-21 ZA ZA200410280A patent/ZA200410280B/en unknown
2005
- 2005-01-13 NO NO20050214A patent/NO20050214L/no not_active Application Discontinuation
- 2005-01-24 MA MA28062A patent/MA27264A1/fr unknown

Also Published As

Publication number	Publication date
AR040462A1 (es)	2005-04-06
GEP20074178B (en)	2007-08-10
WO2004000815A1 (fr)	2003-12-31
MA27264A1 (fr)	2005-03-01
CN1465566A (zh)	2004-01-07
CA2491214A1 (fr)	2003-12-31
KR20050058999A (ko)	2005-06-17
NO20050214L (no)	2005-01-13
PL374039A1 (en)	2005-09-19
BR0312444A (pt)	2005-05-10
KR100677018B1 (ko)	2007-01-31
EA007229B1 (ru)	2006-08-25
NZ537405A (en)	2006-03-31
AU2003242278A1 (en)	2004-01-06
HK1077823A1 (en)	2006-02-24
EP1608625A1 (fr)	2005-12-28
JP2006501174A (ja)	2006-01-12
ZA200410280B (en)	2006-07-26
EA200500081A1 (ru)	2005-06-30
MXPA05000076A (es)	2005-04-08
US20060167076A1 (en)	2006-07-27
CN1303069C (zh)	2007-03-07
CN1675183A (zh)	2005-09-28

Publication	Publication Date	Title
KR100706462B1 (ko)	2007-04-10	시노메닌 및 시노메닌 화합물, 이의 합성 방법 및 용도
FR2674849A1 (fr)	1992-10-09	Nouveaux derives de n-cyclohexyl benzamides ou thiobenzamides, leurs preparations et leurs applications en therapeutique.
SU1563592A3 (ru)	1990-05-07	Способ получени циннолинкарбоксамидов или их фармацевтически приемлемых солей
CA1291994C (fr)	1991-11-12	Derives furo ¬3,2-c\| pyridine, leur preparation et compositions pharmaceutiques en contenant
KR20080032007A (ko)	2008-04-11	신규의 캄토테신 유도체 화합물, 그들의 제조 방법 및 상기화합물을 포함하는 약제학적 조성물
Coomes et al.	1973	Alkaloids of the Papaveraceae. XX. 2, 9-Dimethoxy-3-hydroxypavinane. New alkaloid from Argemone munita subspecies rotundata
NZ242305A (en)	1994-09-27	Pyrido-,pyrrolo-,thieno- and dibenzo-diazepine derivatives; preparatory processes and pharmaceutical compositions
JPH08501548A (ja)	1996-02-20	抗精神病薬としての環状ベンジルアミノ、ベンジルアミド及びベンジルイミド誘導体
JP3224376B2 (ja)	2001-10-29	新規１−アザ−２−アルキル−６−アリール−シクロアルカン化合物類、それらの製造方法及びそれらを含む医薬組成物
KR100677018B1 (ko)	2007-01-31	아쿠투민과 아쿠투민 화합물, 및 이의 합성과 용도
Freed et al.	1976	Bridged aminotetralins. 4. Resolution of potent analgesics of the bridged aminotetralin type
WO2004043952A1 (fr)	2004-05-27	Nouveaux derives de 2,3-dihydro-4(1h)-pyridinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA2383315C (fr)	2008-02-05	Nouveaux derives de pyrimidin-4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2619817A1 (fr)	1989-03-03	Nouvelles beta carbolines 3-substituees, procede et intermediaires de preparation, application a titre de medicaments et compositions pharmaceutiques les renfermant
EP0203902A2 (fr)	1986-12-03	Dérivés de 1,2,3,4,5,6-hexahydro-azépino[4,5-b]indole, leur préparation, composes intermédiaires, et leur application en thérapeutique
FR2781482A1 (fr)	2000-01-28	Nouveaux derives de 8h-thieno-[2,3-b]pyrrolizine-8-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
HU215593B (hu)	1999-01-28	Izopropil-(2-metoxi-etil)-4-(2-klór-3-ciano-fenil)-1,4-dihidro-2,6-dimetil-piridin-3,5-dikarboxilát, eljárás előállítására és ezt tartalmazó gyógyszerkészítmény
JPH0524150B2 (fr)	1993-04-06
JP2011037845A (ja)	2011-02-24	新規ピペリジン化合物、その製造法、およびそれを含有する薬学的組成物
HU203536B (en)	1991-08-28	Process for producing n-(substituted-alkylidene)-condensed bicycloalkano- and tiopyrano-quinolin-amines and pharmaceutical compositions containing them
HK1060126A (en)	2004-07-30	Acutumine and acutumine compounds, synthesis and use
KR20080032006A (ko)	2008-04-11	신규의 캄토테신 유도체 화합물, 그들의 제조 방법 및 상기화합물을 포함하는 약제학적 조성물
CH599226A5 (en)	1978-05-12	Methyl-di:hydro-benzothiadiazine-spiro-piperidine oxide prepn.
HK1154238A (en)	2012-04-13	New piperidine compounds, a process for their preparation and pharmaceutical compositions containing them
HU198942B (en)	1989-12-28	Process for producing new hydrazone derivatives of 3-formylrifamycin and pharmaceutical compositions comprising same