HU210775B - Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl-4h-carbazol-4-one - Google Patents

Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl-4h-carbazol-4-one Download PDF

Info

Publication number: HU210775B
Authority: HU; Hungary
Prior art keywords: methyl; formula; imidazol; acid; tetrahydro
Prior art date: 1992-03-13

Application number

HU9300718A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT64537A (en

HU9300718D0 (en

Inventor

Clotet Juan Huguet

Ges Jose Maria Caldero

Original Assignee

Vita Invest Sa

Sint Quimica 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

1995-07-28

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

1993-05-28 Publication of HU9300718D0 publication Critical patent/HU9300718D0/hu

1994-01-28 Publication of HUT64537A publication Critical patent/HUT64537A/hu

1995-07-28 Publication of HU210775B publication Critical patent/HU210775B/hu

Links

-1 2-methyl-1h-imidazol-1-yl Chemical group 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 9
FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 claims description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 6
238000006798 ring closing metathesis reaction Methods 0.000 claims description 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
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 4
GUXGFEPITRBHDB-UHFFFAOYSA-N 2-[(2-methylimidazol-1-yl)methyl]-4-(1-methylindol-2-yl)butanoic acid Chemical compound CC=1N(C=CN=1)CC(C(=O)O)CCC=1N(C2=CC=CC=C2C=1)C GUXGFEPITRBHDB-UHFFFAOYSA-N 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
239000003377 acid catalyst Substances 0.000 claims 1
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 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 9
239000007787 solid Substances 0.000 description 7
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
238000005160 1H NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
NOOYFQLPKUQDNE-UHFFFAOYSA-N 2-(bromomethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)CBr NOOYFQLPKUQDNE-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
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 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture 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
ZFPUZZSDVPSGFJ-UHFFFAOYSA-N 2-(3-carboxybut-3-enyl)-1-methylindole-3-carboxylic acid Chemical compound C=C(C(=O)O)CCC=1N(C2=CC=CC=C2C=1C(=O)O)C ZFPUZZSDVPSGFJ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
OTAOHVAQDLTDBP-UHFFFAOYSA-N 4-(3-ethoxycarbonyl-1-methylindol-2-yl)-2-methylidenebutanoic acid Chemical compound C=C(C(=O)O)CCC=1N(C2=CC=CC=C2C=1C(=O)OCC)C OTAOHVAQDLTDBP-UHFFFAOYSA-N 0.000 description 1
DNEFVEWFSTYRNM-UHFFFAOYSA-N 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-1,2,3,4-tetrahydrocarbazole Chemical compound CC1=NC=CN1CC1CC(C=2C(=CC=CC=2)N2C)=C2CC1 DNEFVEWFSTYRNM-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
206010028813 Nausea 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
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
230000001149 cognitive effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 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
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000007522 mineralic acids Chemical group 0.000 description 1
230000008693 nausea Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

HU9300718A 1992-03-13 1993-03-12 Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl-4h-carbazol-4-one HU210775B (en)

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 (3)

Publication Number	Publication Date
HU9300718D0 HU9300718D0 (en)	1993-05-28
HUT64537A HUT64537A (en)	1994-01-28
HU210775B true HU210775B (en)	1995-07-28

Family

ID=8276385

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU9300718A HU210775B (en)	1992-03-13	1993-03-12	Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl-4h-carbazol-4-one

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
LU88268I2 (de) *	1984-01-25	1994-02-03
GB8518743D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Heterocyclic compounds
GB8518742D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Process
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 CZ CZ93396A patent/CZ281753B6/cs not_active IP Right Cessation
- 1993-03-10 EG EG14493A patent/EG20262A/xx active
- 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 PT PT101216A patent/PT101216B/pt not_active IP Right Cessation
- 1993-03-11 NO NO930887A patent/NO300973B1/no not_active IP Right Cessation
- 1993-03-11 AR AR93324474A patent/AR248019A1/es active
- 1993-03-12 AT AT0048793A patent/AT402730B/de not_active IP Right Cessation
- 1993-03-12 HU HU9300718A patent/HU210775B/hu 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
- 1993-03-12 RU RU93004833/04A patent/RU2109741C1/ru not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO930887L (no)	1993-09-14
PL170751B1 (pl)	1997-01-31
FI931104A0 (fi)	1993-03-12
GR930100094A (el)	1993-11-30
NO300973B1 (no)	1997-08-25
AT402730B (de)	1997-08-25
RU2109741C1 (ru)	1998-04-27
IS1783B (is)	2001-10-22
IS3985A (is)	1993-09-14
HUT64537A (en)	1994-01-28
PL298037A1 (en)	1993-12-27
SK278786B6 (sk)	1998-02-04
PT101216B (pt)	1999-10-29
ES2043535B1 (es)	1994-08-01
EG20262A (en)	1998-05-31
AR248019A1 (es)	1995-05-31
PT101216A (pt)	1994-03-31
ES2043535A1 (es)	1993-12-16
FI931104L (fi)	1993-09-14
FI105098B (fi)	2000-06-15
HU9300718D0 (en)	1993-05-28
KR100277414B1 (ko)	2001-01-15
KR930019665A (ko)	1993-10-18
CZ39693A3 (en)	1994-01-19
CZ281753B6 (cs)	1997-01-15
ATA48793A (de)	1996-12-15
SK16993A3 (en)	1993-11-10
NO930887D0 (no)	1993-03-11

Legal Events

Date	Code	Title	Description
1999-03-29	HPC4	Succession in title of patentee	Owner name: VITA-INVEST, S.A., ES
2003-05-28	HPC4	Succession in title of patentee	Owner name: LABORATORIOS VITA, S.A., ES
2005-06-28	HPC4	Succession in title of patentee	Owner name: VITA CIENTIFICA, ES
2007-12-28	GB9A	Succession in title	Owner name: INKE, S.A., ES Free format text: FORMER OWNER(S): QUIMICA SINTETICA S.A., ES; VITA-INVEST S.A., ES; LABORATORIOS VITA, S.A., ES; VITA-INVEST, S.A., ES; VITA CIENTIFICA, ES
2011-12-28	MM4A	Lapse of definitive patent protection due to non-payment of fees

Publication	Publication Date	Title
JPH0653736B2 (ja)	1994-07-20	新規な酸性インド−ル化合物
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