PL170751B1 - 4H-karbazolonu-4 PL - Google Patents

4H-karbazolonu-4 PL

Info

Publication number: PL170751B1
Authority: PL; Poland
Prior art keywords: methyl; formula; acid; carbazolone; preparation
Prior art date: 1992-03-13

Application number

PL93298037A

Other languages

English (en)

Polish (pl)

Other versions

PL298037A1 (en

Inventor

Clotet Juan Huguet

Ges Jose Maria Caldero

Original Assignee

Sint Quimica Sa

Vita Invest Sa

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.)

1992-03-13

Filing date

1993-03-12

Publication date

1997-01-31

1993-03-12 Application filed by Sint Quimica Sa, Vita Invest Sa filed Critical Sint Quimica Sa

1993-12-27 Publication of PL298037A1 publication Critical patent/PL298037A1/xx

1997-01-31 Publication of PL170751B1 publication Critical patent/PL170751B1/pl

Links

238000000034 method Methods 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
239000002904 solvent Substances 0.000 claims abstract description 7
230000003213 activating effect Effects 0.000 claims abstract description 3
238000007171 acid catalysis Methods 0.000 claims abstract 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
238000007363 ring formation reaction Methods 0.000 claims description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 5
239000003377 acid catalyst Substances 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract description 12
238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
238000005917 acylation reaction Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
239000000203 mixture Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
AMLYRCOEFHJSFS-UHFFFAOYSA-N carbazol-1-one Chemical compound C1=CC=C2C3=CC=CC(=O)C3=NC2=C1 AMLYRCOEFHJSFS-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
NOOYFQLPKUQDNE-UHFFFAOYSA-N 2-(bromomethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)CBr NOOYFQLPKUQDNE-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
102000035037 5-HT3 receptors Human genes 0.000 description 1
108091005477 5-HT3 receptors Proteins 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
RQRUAENQOVZHNW-UHFFFAOYSA-N ethyl 1,2-dimethylindole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(C)N(C)C2=C1 RQRUAENQOVZHNW-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

PL93298037A 1992-03-13 1993-03-12 4H-karbazolonu-4 PL PL170751B1 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES09200552A ES2043535B1 (es)	1992-03-13	1992-03-13	Procedimiento para la obtencion de la 1,2,3,9-tetrahidro-9-metil-3-(2-metil-1h-imidazol-1-il)metil*-4h-carbazol-4-ona.

Publications (2)

Publication Number	Publication Date
PL298037A1 PL298037A1 (en)	1993-12-27
PL170751B1 true PL170751B1 (pl)	1997-01-31

Family

ID=8276385

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL93298037A PL170751B1 (pl)	1992-03-13	1993-03-12	4H-karbazolonu-4 PL

Country Status (15)

Country	Link
KR (1)	KR100277414B1 (de)
AR (1)	AR248019A1 (de)
AT (1)	AT402730B (de)
CZ (1)	CZ281753B6 (de)
EG (1)	EG20262A (de)
ES (1)	ES2043535B1 (de)
FI (1)	FI105098B (de)
GR (1)	GR930100094A (de)
HU (1)	HU210775B (de)
IS (1)	IS1783B (de)
NO (1)	NO300973B1 (de)
PL (1)	PL170751B1 (de)
PT (1)	PT101216B (de)
RU (1)	RU2109741C1 (de)
SK (1)	SK278786B6 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100368895B1 (ko) *	2000-03-30	2003-01-24	하나제약 주식회사	1,2,3,9-테트라하이드로-9-메틸-3-[(2-메틸-1ｈ-이미다졸-1-일)메틸]-4ｈ-카바졸-4-온의 제조방법
RU2207340C2 (ru) *	2001-08-10	2003-06-27	Ципла Лтд.	Способ получения 1,2,3,9-тетрагидро-9-метил-3-[(2-метил-1н-имидазол-1-ил)метил]-4н-карбазол -4-она или его фармацевтически приемлемых солей

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE460359B (sv) *	1984-01-25	1989-10-02	Glaxo Group Ltd	3-imidazolylmetyltetrahydrokarbazoloner, foerfarande foer framstaellning av dessa och en farmaceutisk komposition
GB8518742D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Process
GB8518743D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Heterocyclic compounds
GB8518741D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Process
GB8617994D0 (en) *	1986-07-23	1986-08-28	Glaxo Group Ltd	Heterocyclic compounds

1992
- 1992-03-13 ES ES09200552A patent/ES2043535B1/es not_active Expired - Fee Related
1993
- 1993-03-08 SK SK169-93A patent/SK278786B6/sk not_active IP Right Cessation
- 1993-03-09 GR GR930100094A patent/GR930100094A/el not_active IP Right Cessation
- 1993-03-10 EG EG14493A patent/EG20262A/xx active
- 1993-03-10 CZ CZ93396A patent/CZ281753B6/cs not_active IP Right Cessation
- 1993-03-11 IS IS3985A patent/IS1783B/is unknown
- 1993-03-11 KR KR1019930003609A patent/KR100277414B1/ko not_active Expired - Fee Related
- 1993-03-11 NO NO930887A patent/NO300973B1/no not_active IP Right Cessation
- 1993-03-11 AR AR93324474A patent/AR248019A1/es active
- 1993-03-11 PT PT101216A patent/PT101216B/pt not_active IP Right Cessation
- 1993-03-12 HU HU9300718A patent/HU210775B/hu not_active IP Right Cessation
- 1993-03-12 RU RU93004833/04A patent/RU2109741C1/ru not_active IP Right Cessation
- 1993-03-12 AT AT0048793A patent/AT402730B/de not_active IP Right Cessation
- 1993-03-12 FI FI931104A patent/FI105098B/fi not_active IP Right Cessation
- 1993-03-12 PL PL93298037A patent/PL170751B1/pl not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT101216A (pt)	1994-03-31
AT402730B (de)	1997-08-25
ES2043535B1 (es)	1994-08-01
SK278786B6 (sk)	1998-02-04
HU210775B (en)	1995-07-28
PT101216B (pt)	1999-10-29
CZ39693A3 (en)	1994-01-19
FI105098B (fi)	2000-06-15
ATA48793A (de)	1996-12-15
GR930100094A (el)	1993-11-30
NO300973B1 (no)	1997-08-25
HU9300718D0 (en)	1993-05-28
RU2109741C1 (ru)	1998-04-27
FI931104A0 (fi)	1993-03-12
PL298037A1 (en)	1993-12-27
NO930887L (no)	1993-09-14
KR100277414B1 (ko)	2001-01-15
KR930019665A (ko)	1993-10-18
HUT64537A (en)	1994-01-28
ES2043535A1 (es)	1993-12-16
AR248019A1 (es)	1995-05-31
NO930887D0 (no)	1993-03-11
IS3985A (is)	1993-09-14
EG20262A (en)	1998-05-31
FI931104L (fi)	1993-09-14
SK16993A3 (en)	1993-11-10
CZ281753B6 (cs)	1997-01-15
IS1783B (is)	2001-10-22

Legal Events

Date	Code	Title	Description
2012-05-31	LAPS	Decisions on the lapse of the protection rights	Effective date: 20110312

Publication	Publication Date	Title
AU707282B2 (en)	1999-07-08	Benzopyran derivatives having leukotriene-antagonistic action
US4739072A (en)	1988-04-19	Process for preparing tetrahydrocarbazolones
ITMI981670A1 (it)	2000-01-21	Derivati ftalazinici inibitori della fosfodiesterasi 4
US5478949A (en)	1995-12-26	Process for preparing ondansetron
US4263437A (en)	1981-04-21	Acetic acid derivatives of 5,6-dihydrobenzo[b]pyrido[3,2-f]thiepine and oxepine
HU195488B (en)	1988-05-30	Process for producing quinolon-carboxylic acid-nitril derivatives
US4910212A (en)	1990-03-20	Heterocyclic compounds
Baraznenok et al.	1999	3‐Trifloxy‐3‐trifluoromethylpropeniminium Triflate: Reaction with Aromatic Amines–An Efficient Synthesis of 2‐Trifluoromethylquinolines
US3784600A (en)	1974-01-08	4-substituted coumarins
Andrews et al.	1993	Pyrrole-2, 3-quinodimethane analogues in the synthesis of indoles. Part 2.1 Synthesis and diels-alder reactions of 1, 6-dihydropyrano [4, 3-b] pyrrol-6 (1H)-ones
PL170751B1 (pl)	1997-01-31	4H-karbazolonu-4 PL
US4350813A (en)	1982-09-21	Process for producing 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone and its intermediates
SU1739848A3 (ru)	1992-06-07	Способ получени производных тианафтена или их фармацевтически приемлемых солей
US3004983A (en)	1961-10-17	4-aminopyrazolo [3, 4-a] indene derivatives
CS214806B2 (en)	1982-06-25	Method of making the derivatives of the auron
EP0142754A2 (de)	1985-05-29	2-Substituierte, eine Imidazolylgruppe tragende Benzoesäuren, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
US4464532A (en)	1984-08-07	Intermediates of 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone
EP0255178A2 (de)	1988-02-03	Verfahren zur Herstellung von Heteroaryl- und Arylalkansäuren
US4677228A (en)	1987-06-30	Chemical process
US20060058532A1 (en)	2006-03-16	Process for the scalable synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]-indole derivatives
PL114404B1 (en)	1981-01-31	Process for manufacturing novel pyrrole derivatives
EP0125937A2 (de)	1984-11-21	2-(2'-Indenyl)-imidazoline, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
Zepeda et al.	1992	Fischer indole synthesis of (β-oxo) indol-3-yl ketones using protected 1, 3-dicarbonyl compounds
PL198521B1 (pl)	2008-06-30	Sposób wytwarzania pochodnych spiro [(4-cykloheksanono)-[3H]indol]-2'[1'H]-onu oraz związki pośrednie
US4798893A (en)	1989-01-17	Process for producing 1-(5-substituted-2-ethynylphenyl)-2-propanones