NO794271L - Fremgangsmaate for fremstilling av indol-dioner - Google Patents

Fremgangsmaate for fremstilling av indol-dioner

Info

Publication number: NO794271L
Authority: NO; Norway
Prior art keywords: alkyl; compounds; cycloalkyl; compound; pyrimido
Prior art date: 1979-04-26

Application number

NO794271A

Other languages

English (en)

Norwegian (no)

Inventor

Gabor Istvan Koletar

Jonathan Frost

Regis Dupont

Patrick Lardenois

Claude Morel

Henry Najer

Original Assignee

Synthelabo

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.)

1979-04-26

Filing date

1979-12-27

Publication date

1980-10-28

1979-12-27 Application filed by Synthelabo filed Critical Synthelabo

1980-10-28 Publication of NO794271L publication Critical patent/NO794271L/no

Links

238000000034 method Methods 0.000 title description 6
238000004519 manufacturing process Methods 0.000 title description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract description 30
125000000217 alkyl group Chemical group 0.000 abstract description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
206010002660 Anoxia Diseases 0.000 abstract description 5
206010021143 Hypoxia Diseases 0.000 abstract description 5
125000003545 alkoxy group Chemical group 0.000 abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
AMBZNXNKAKZDHN-UHFFFAOYSA-N 3,10,12,14-tetrazatetracyclo[7.7.0.02,6.011,15]hexadeca-1,3,5,7,9,11,13,15-octaene Chemical class C1=C2N=CN=C2N=C2C=CC3=CC=NC3=C21 AMBZNXNKAKZDHN-UHFFFAOYSA-N 0.000 abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
238000010438 heat treatment Methods 0.000 abstract description 2
-1 R2=H Chemical group 0.000 abstract 1
230000002378 acidificating effect Effects 0.000 abstract 1
229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
239000004089 psychotropic agent Substances 0.000 abstract 1
238000002560 therapeutic procedure Methods 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
238000010992 reflux Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000976983 Anoxia Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
230000007953 anoxia Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000007958 sleep Effects 0.000 description 3
XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000003756 stirring Methods 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 1
206010062519 Poor quality sleep Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000006399 behavior Effects 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
230000006931 brain damage Effects 0.000 description 1
231100000874 brain damage Toxicity 0.000 description 1
208000029028 brain injury Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000517 effect on sleep Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
230000004617 sleep duration Effects 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
208000009999 tuberous sclerosis Diseases 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- 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
- 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
- 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
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO794271A 1979-04-26 1979-12-27 Fremgangsmaate for fremstilling av indol-dioner NO794271L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7910653A FR2455039A1 (fr)	1979-04-26	1979-04-26	Pyrimido et imidazo-pyrido-indole-diones et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
NO794271L true NO794271L (no)	1980-10-28

Family

ID=9224796

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO794271A NO794271L (no)	1979-04-26	1979-12-27	Fremgangsmaate for fremstilling av indol-dioner

Country Status (15)

Country	Link
US (1)	US4358451A (th)
EP (1)	EP0018857B1 (th)
JP (1)	JPS55145689A (th)
AT (1)	ATE2253T1 (th)
AU (1)	AU528634B2 (th)
CA (1)	CA1129854A (th)
DE (1)	DE3061648D1 (th)
DK (1)	DK16980A (th)
ES (1)	ES487713A1 (th)
FR (1)	FR2455039A1 (th)
GR (1)	GR74394B (th)
IL (1)	IL59128A (th)
NO (1)	NO794271L (th)
PT (1)	PT70698A (th)
ZA (1)	ZA80242B (th)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3246932A1 (de) *	1982-12-16	1984-06-20	Schering AG, 1000 Berlin und 4709 Bergkamen	Substituierte 5h-pyrimido(5,4-b)indole
CA2450073C (en)	2001-07-25	2017-08-29	Biomarin Pharmaceutical Inc.	Compositions and methods for modulating blood-brain barrier transport
US7595311B2 (en)	2002-05-24	2009-09-29	Exelixis, Inc.	Azepinoindole derivatives as pharmaceutical agents
TWI329111B (en) *	2002-05-24	2010-08-21	X Ceptor Therapeutics Inc	Azepinoindole and pyridoindole derivatives as pharmaceutical agents
EP2671508B1 (en)	2005-04-28	2020-09-16	Proteus Digital Health, Inc.	Pharma-informatics system
FR2901795A1 (fr) *	2006-05-30	2007-12-07	Fourtillan Snc	Derives de pyrimidino[1',6'-1,2]pyrido[3,4-b]indoles et leur utilisation en therapeutique
JP2010503710A (ja)	2006-09-18	2010-02-04	ラプトールファーマシューティカルインコーポレイテッド	受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置
ES2919563T3 (es)	2009-02-20	2022-07-27	Enhanx Biopharm Inc	Sistema de administración de medicamentos a base de glutatión
KR20180114970A (ko)	2009-05-06	2018-10-19	라보라토리 스킨 케어, 인크.	활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1076114A (en) *	1975-02-10	1980-04-22	Mitsubishi Chemical Industries Limited	1,5-alkylene-3-aryl hydantoin derivatives

1979
- 1979-04-26 FR FR7910653A patent/FR2455039A1/fr active Granted
- 1979-12-27 NO NO794271A patent/NO794271L/no unknown
1980
- 1980-01-14 JP JP300380A patent/JPS55145689A/ja active Pending
- 1980-01-15 IL IL59128A patent/IL59128A/xx unknown
- 1980-01-15 GR GR60963A patent/GR74394B/el unknown
- 1980-01-15 ZA ZA00800242A patent/ZA80242B/xx unknown
- 1980-01-15 DE DE8080400050T patent/DE3061648D1/de not_active Expired
- 1980-01-15 AU AU54630/80A patent/AU528634B2/en not_active Ceased
- 1980-01-15 CA CA343,698A patent/CA1129854A/en not_active Expired
- 1980-01-15 AT AT80400050T patent/ATE2253T1/de not_active IP Right Cessation
- 1980-01-15 DK DK16980A patent/DK16980A/da not_active Application Discontinuation
- 1980-01-15 ES ES487713A patent/ES487713A1/es not_active Expired
- 1980-01-15 US US06/112,238 patent/US4358451A/en not_active Expired - Lifetime
- 1980-01-15 EP EP80400050A patent/EP0018857B1/fr not_active Expired
- 1980-01-15 PT PT70698A patent/PT70698A/pt unknown

Also Published As

Publication number	Publication date
ZA80242B (en)	1980-12-31
DE3061648D1 (en)	1983-02-24
IL59128A (en)	1982-07-30
EP0018857B1 (fr)	1983-01-19
EP0018857A1 (fr)	1980-11-12
AU528634B2 (en)	1983-05-05
PT70698A (fr)	1980-02-01
ES487713A1 (es)	1980-06-16
JPS55145689A (en)	1980-11-13
AU5463080A (en)	1980-10-30
DK16980A (da)	1980-10-27
CA1129854A (en)	1982-08-17
ATE2253T1 (de)	1983-02-15
IL59128A0 (en)	1980-05-30
GR74394B (th)	1984-06-28
FR2455039B1 (th)	1983-05-13
FR2455039A1 (fr)	1980-11-21
US4358451A (en)	1982-11-09

Publication	Publication Date	Title
SU1068037A3 (ru)	1984-01-15	Способ получени производных 3-(1-пиперидинилалкил)-4 @ -пиридо/1,2- @ / пиримидин-4-она или их фармацевтически приемлимых кислотно-аддитивных солей
DE60122767T2 (de)	2007-09-13	Indoly-lsulphonyl-verbindungen zur behandlung von störungen des zns
DK174161B1 (da)	2002-07-29	Anellerede indolderivater, fremgangsmåde til deres fremstilling og fremgangsmåde til fremstilling af farmaceutisk præparat indeholdende dem
US3072530A (en)	1963-01-08	Therapeutic indoles for psychic stimulation and relief of mental depression
FR2619111A1 (fr)	1989-02-10	Derives de (piperidinyl-4)methyl-2 tetrahydro-1,2,3,4 9h-pyrido (3,4-b) indole, leur preparation et leur application en therapeutique
NO873432L (no)	1988-02-16	Fremgangsmaate for fremstilling av imidazolforbindelser.
CA2476757A1 (en)	2003-09-12	Nitrogen-containing heterocyclic compound
JP2008538550A (ja)	2008-10-30	ウイルス感染および腫瘍性疾患を処置するためのサイトカイン生合成の調節因子としての１−置換ピラゾロ（３，４−ｃ）環状化合物
NZ264596A (en)	1995-11-27	Imidazol-4-ylpiperidines; compounds, preparation and pharmaceutical compositions containing them
SU978730A3 (ru)	1982-11-30	Способ получени этилового эфира 9-фенилгидразоно-6-метил-4-оксо-6,7,8,9-тетрагидро-4н-пиридо/1,2-а/-пиримидин-3-карбоновой кислоты
US4277476A (en)	1981-07-07	Derivatives of fluorenes and fluoranthenes and process for their preparation
US4336256A (en)	1982-06-22	Pyridoindole derivatives
US4358451A (en)	1982-11-09	Pyrimido- and imidazo-pyridoindole derivatives
EP0255217B1 (en)	1992-01-22	Fused imidazoheterocyclic compounds
EP0062580B1 (fr)	1985-11-06	Dérivés de l'imidazo(1,2-a)quinoléines
GB2290292A (en)	1995-12-20	2-Phenylpyridazino[4,5-b]indole-1,4-dione derivatives as NMDA and AMPA antagonists
US4482714A (en)	1984-11-13	Pyrazino[2',3'-3,4]pyrido[1,2-a]indole derivatives
US4757070A (en)	1988-07-12	3-oxadiazolyl-5-aminoalkyl-beta-carboline derivatives compositions and use
FR2898358A1 (fr)	2007-09-14	Association d'un antagoniste du recepteur 5ht2 et d'activateur du recepteur 5ht2 par modulation allosterique et leurs utilisations comme produits medicaux
JPH0764844B2 (ja)	1995-07-12	ピリダジノピロロイソキノリン誘導体
MXPA04001810A (es)	2004-07-08	Compuestos de aminopirrol como agentes antiinflamatorios.
US3280145A (en)	1966-10-18	New indole derivatives and their acid addition salts
US4515949A (en)	1985-05-07	[2-(1H-indol-1-yl)ethyl]-2-piperazine and pyrido[1,2-a]indol-9-one as intermediates for pyrazino(2,3-3,4)pyrido(1,2-a) indoles which are useful for treating hypertension in mammals
CA1162544A (en)	1984-02-21	Naphthyridine derivatives
US4061752A (en)	1977-12-06	6-Piperazino-11-methylene-dibenzazepines[b,e]