UA75141C2 - Dihydroimidazo[5,l-a]- -carboline derivatives, a method for the preparation thereof and a pharmaceutical composition based thereon - Google Patents

Dihydroimidazo[5,l-a]- -carboline derivatives, a method for the preparation thereof and a pharmaceutical composition based thereon Download PDF

Info

Publication number: UA75141C2
Authority: UA; Ukraine
Prior art keywords: linear; branched; dihydroimidazo; carbolinemethanesulfonate; alkyl
Prior art date: 2001-05-16

Application number

UA20031211614A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Macef

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.)

2001-05-16

Filing date

2002-05-16

Publication date

2006-03-15

2002-05-16 Application filed by Macef filed Critical Macef

2006-03-15 Publication of UA75141C2 publication Critical patent/UA75141C2/uk

Links

238000000034 method Methods 0.000 title claims description 30
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 42
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
230000000147 hypnotic effect Effects 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
239000003814 drug Substances 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 4
230000000996 additive effect Effects 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
230000003993 interaction Effects 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
108090000765 processed proteins & peptides Proteins 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
-1 trihalogenoalkyl Chemical group 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 2
125000003710 aryl alkyl group Chemical group 0.000 abstract 2
125000002252 acyl group Chemical group 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000003282 alkyl amino group Chemical group 0.000 abstract 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 24
238000004949 mass spectrometry Methods 0.000 description 22
239000000758 substrate Substances 0.000 description 22
JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 description 18
150000001408 amides Chemical class 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000007363 ring formation reaction Methods 0.000 description 12
229940097276 5-methoxytryptamine Drugs 0.000 description 9
241000287828 Gallus gallus Species 0.000 description 8
235000013330 chicken meat Nutrition 0.000 description 8
241000282472 Canis lupus familiaris Species 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
206010062519 Poor quality sleep Diseases 0.000 description 6
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 6
239000002168 alkylating agent Substances 0.000 description 5
229940100198 alkylating agent Drugs 0.000 description 5
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
206010041349 Somnolence Diseases 0.000 description 4
230000000803 paradoxical effect Effects 0.000 description 4
239000000902 placebo Substances 0.000 description 4
229940068196 placebo Drugs 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
230000037361 pathway Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000243 solution Substances 0.000 description 3
241000894007 species Species 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
230000008859 change Effects 0.000 description 2
238000010908 decantation Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
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 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000005046 dihydronaphthyl group Chemical group 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000035622 drinking Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000004424 eye movement Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000002454 frontal bone Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
210000003128 head Anatomy 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000002674 ointment Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000008667 sleep stage Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002557 soporific effect Effects 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D471/12—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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Anesthesiology (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UA20031211614A 2001-05-16 2002-05-16 Dihydroimidazo[5,l-a]- -carboline derivatives, a method for the preparation thereof and a pharmaceutical composition based thereon UA75141C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0106444A FR2824829B1 (fr)	2001-05-16	2001-05-16	Nouveaux derives de dihydroimidazo [5,1-a]-beta-carboline, leur procede de preparation et leur application a titre de medicament
PCT/FR2002/001653 WO2002092598A1 (fr)	2001-05-16	2002-05-16	DERIVES DE DIHYDROIMIDAZO [5,1-A]-β-CARBOLINE, LEUR PROCEDE DE PREPARATION ET LEUR APPLICATION A TITRE DE MEDICAMENT

Publications (1)

Publication Number	Publication Date
UA75141C2 true UA75141C2 (en)	2006-03-15

Family

ID=8863340

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20031211614A UA75141C2 (en)	2001-05-16	2002-05-16	Dihydroimidazo[5,l-a]- -carboline derivatives, a method for the preparation thereof and a pharmaceutical composition based thereon

Country Status (24)

Country	Link
US (1)	US7291627B2 (is)
EP (1)	EP1390367B1 (is)
JP (1)	JP2004535399A (is)
CN (1)	CN1254476C (is)
AT (1)	ATE400575T1 (is)
AU (1)	AU2002313058B2 (is)
BG (1)	BG108423A (is)
BR (1)	BR0209679A (is)
CA (1)	CA2447588A1 (is)
CZ (1)	CZ20033346A3 (is)
DE (1)	DE60227506D1 (is)
FR (1)	FR2824829B1 (is)
HU (1)	HUP0400304A2 (is)
IL (1)	IL158839A0 (is)
IS (1)	IS7034A (is)
MX (1)	MXPA03010506A (is)
NO (1)	NO20035026D0 (is)
NZ (1)	NZ530054A (is)
PL (1)	PL367073A1 (is)
RU (1)	RU2298010C2 (is)
SK (1)	SK15412003A3 (is)
UA (1)	UA75141C2 (is)
WO (1)	WO2002092598A1 (is)
ZA (1)	ZA200309496B (is)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2908768A1 (fr) *	2006-06-19	2008-05-23	Fourtillan Snc	DERIVES DE 3H,11H-OXAZOLO (3',4':1,2)PYRIDO(3,4-b)INDOLE ET LEUR UTILISATION EN THERAPEUTIQUE
FR2904973A1 (fr) *	2006-08-18	2008-02-22	Fourtillan Snc	Derives de 1-methylidene-pyrido[3,4-b]indole et leur utilisation en therapeutique.
FR2912405A1 (fr) *	2007-02-08	2008-08-15	Fourtillan Snc	Derives des imidazo[1',5':1,6]pyrido[3,4-b]indoles et leur utilisation en therapeutique
FR2916200A1 (fr) *	2007-05-18	2008-11-21	Fourtillan Snc	Nouveaux derives des 1,2,3,4,6,7,12,12a-octahydro pyrazino[1',2':1,6]pyrido[3,4-b]indoles, leur preparation et leur utilisation en therapeutique

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9401090D0 (en) *	1994-01-21	1994-03-16	Glaxo Lab Sa	Chemical compounds
US5631265A (en) *	1994-03-11	1997-05-20	Eli Lilly And Company	8-substituted tetrahydro-beta-carbolines
FR2724384B1 (fr) *	1994-09-14	1999-04-16	Cemaf	Nouveaux derives de la 3,4-dihydro beta-carboline agonistes de la melatonine, leur procede de preparation et leur utilisation a titre de medicament
TR200003596T2 (tr) *	1998-03-17	2001-04-20	Macef	Hipnotik beta-karbolin türevleri,hazırlanmaları için işlem ve tıbbi ürün olarak kullanımları

2001
- 2001-05-16 FR FR0106444A patent/FR2824829B1/fr not_active Expired - Fee Related
2002
- 2002-05-16 US US10/478,002 patent/US7291627B2/en not_active Expired - Fee Related
- 2002-05-16 PL PL02367073A patent/PL367073A1/xx not_active Application Discontinuation
- 2002-05-16 DE DE60227506T patent/DE60227506D1/de not_active Expired - Fee Related
- 2002-05-16 RU RU2003136163/04A patent/RU2298010C2/ru not_active IP Right Cessation
- 2002-05-16 MX MXPA03010506A patent/MXPA03010506A/es active IP Right Grant
- 2002-05-16 IL IL15883902A patent/IL158839A0/xx unknown
- 2002-05-16 NZ NZ530054A patent/NZ530054A/en unknown
- 2002-05-16 WO PCT/FR2002/001653 patent/WO2002092598A1/fr not_active Ceased
- 2002-05-16 AU AU2002313058A patent/AU2002313058B2/en not_active Ceased
- 2002-05-16 EP EP02738249A patent/EP1390367B1/fr not_active Expired - Lifetime
- 2002-05-16 AT AT02738249T patent/ATE400575T1/de not_active IP Right Cessation
- 2002-05-16 BR BR0209679-0A patent/BR0209679A/pt not_active IP Right Cessation
- 2002-05-16 JP JP2002589482A patent/JP2004535399A/ja active Pending
- 2002-05-16 CN CNB028137973A patent/CN1254476C/zh not_active Expired - Fee Related
- 2002-05-16 CA CA002447588A patent/CA2447588A1/fr not_active Abandoned
- 2002-05-16 CZ CZ20033346A patent/CZ20033346A3/cs unknown
- 2002-05-16 HU HU0400304A patent/HUP0400304A2/hu unknown
- 2002-05-16 SK SK1541-2003A patent/SK15412003A3/sk unknown
- 2002-05-16 UA UA20031211614A patent/UA75141C2/uk unknown
2003
- 2003-11-12 NO NO20035026A patent/NO20035026D0/no not_active Application Discontinuation
- 2003-11-13 IS IS7034A patent/IS7034A/is unknown
- 2003-12-08 BG BG108423A patent/BG108423A/xx unknown
- 2003-12-08 ZA ZA200309496A patent/ZA200309496B/xx unknown

Also Published As

Publication number	Publication date
DE60227506D1 (de)	2008-08-21
MXPA03010506A (es)	2005-03-07
FR2824829A1 (fr)	2002-11-22
CZ20033346A3 (cs)	2007-12-27
AU2002313058B2 (en)	2007-03-22
EP1390367B1 (fr)	2008-07-09
ZA200309496B (en)	2004-08-17
RU2003136163A (ru)	2005-05-20
US7291627B2 (en)	2007-11-06
CA2447588A1 (fr)	2002-11-21
FR2824829B1 (fr)	2005-06-03
BG108423A (en)	2004-12-30
JP2004535399A (ja)	2004-11-25
CN1254476C (zh)	2006-05-03
NO20035026D0 (no)	2003-11-12
US20060089372A1 (en)	2006-04-27
EP1390367A1 (fr)	2004-02-25
IS7034A (is)	2003-11-13
HUP0400304A2 (hu)	2004-09-28
SK15412003A3 (sk)	2004-06-08
RU2298010C2 (ru)	2007-04-27
CN1525973A (zh)	2004-09-01
PL367073A1 (en)	2005-02-21
NZ530054A (en)	2005-12-23
BR0209679A (pt)	2004-09-14
ATE400575T1 (de)	2008-07-15
IL158839A0 (en)	2004-05-12
WO2002092598A1 (fr)	2002-11-21

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