CA2106642A1 - Carbazolone derivatives and process for preparing the same - Google Patents

Carbazolone derivatives and process for preparing the same

Info

Publication number
CA2106642A1
CA2106642A1 CA002106642A CA2106642A CA2106642A1 CA 2106642 A1 CA2106642 A1 CA 2106642A1 CA 002106642 A CA002106642 A CA 002106642A CA 2106642 A CA2106642 A CA 2106642A CA 2106642 A1 CA2106642 A1 CA 2106642A1
Authority
CA
Canada
Prior art keywords
formula
methyl
group
same
preparing
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002106642A
Other languages
French (fr)
Other versions
CA2106642C (en
Inventor
Peter Bod
Kalman Harsanyi
Ferenc Trischler
Eva Fekecs
Attila Csehi
Bela Hegedus
Eva Mersich
Gyorgyi Szabo
Erika Horvath
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Richter Gedeon Vegyeszeti Gyar Nyrt
Original Assignee
Richter Gedeon Vegyeszeti Gyar RT
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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26318102&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2106642(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from HU9203222A external-priority patent/HU212934B/en
Priority claimed from HU9203223A external-priority patent/HU212785B/en
Application filed by Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT
Publication of CA2106642A1 publication Critical patent/CA2106642A1/en
Application granted granted Critical
Publication of CA2106642C publication Critical patent/CA2106642C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/06Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • C07D209/82Carbazoles; Hydrogenated carbazoles
    • C07D209/88Carbazoles; 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

Abstract

The invention relates to carbazolone derivatives of the formula wherein A represents a group of formula wherein R represents a hydroxyl or 2-methyl-1H-imidazol-1-yl group;
B represents a group of formula wherein R1 represents hydrogen or a methyl or ethyl group; or A and B together form a group of formula wherein R2 means a methyl or ethyl group; or A and B together form a group of formula The above compounds are useful intermediates in the: syn-thesis of ondansetron of formula chemically 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]--1,2,3,9-tetrahydro-4H-carbazol-4-one.
The invention further relates to a novel process for the preparation of compounds of the formula (I), wherein A and B
are the same as in formula (I) but B may be also hydrogen.
Thus, this novel process is suitable for the preparation of ondansetron itself.
CA002106642A 1992-10-14 1993-09-21 Carbazolone derivatives and process for preparing the same Expired - Fee Related CA2106642C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
HU9203222A HU212934B (en) 1992-10-14 1992-10-14 Process for producing novel alkoxalylated carbazolone derivatives
HU3223/92 1992-10-14
HU9203223A HU212785B (en) 1992-10-14 1992-10-14 Process for producing of a carbazolone derivative
HU3222/92 1992-10-14

Publications (2)

Publication Number Publication Date
CA2106642A1 true CA2106642A1 (en) 1994-04-15
CA2106642C CA2106642C (en) 2005-08-16

Family

ID=26318102

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002106642A Expired - Fee Related CA2106642C (en) 1992-10-14 1993-09-21 Carbazolone derivatives and process for preparing the same

Country Status (20)

Country Link
US (2) US5416221A (en)
EP (1) EP0595111B2 (en)
JP (1) JP3378315B2 (en)
KR (1) KR100289912B1 (en)
CN (2) CN1052979C (en)
AT (1) ATE157973T1 (en)
CA (1) CA2106642C (en)
CZ (1) CZ284223B6 (en)
DE (1) DE69313771T3 (en)
DK (1) DK0595111T4 (en)
EE (1) EE03071B1 (en)
ES (1) ES2106936T5 (en)
GR (1) GR3025599T3 (en)
HR (1) HRP931292B1 (en)
PL (2) PL174173B1 (en)
RO (1) RO115799B1 (en)
RU (1) RU2119914C1 (en)
SI (1) SI9300537B (en)
SK (1) SK281243B6 (en)
UA (2) UA26893C2 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU226135B1 (en) * 2000-03-28 2008-05-28 Richter Gedeon Nyrt Intermediate of ondansetron and process for its production
KR100368895B1 (en) * 2000-03-30 2003-01-24 하나제약 주식회사 A process for preparing 1,2,3,9-tetrahydro-9-methyl-3- [(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one
HUP0401239A2 (en) * 2000-10-30 2004-12-28 Teva Pharmaceutical Industries Ltd. Novel crystal and solvate forms of ondansetron hydrochloride and processes for their preparation
EP1207160A1 (en) * 2000-11-20 2002-05-22 Hanmi Pharm. Co., Ltd. Process for the preparation of 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)-methyl)-4H-carbazol-4-one
CA2483566A1 (en) * 2002-04-29 2003-11-13 Biogal Gyogyszergyar Rt. Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl]-4h-carbazol-4-one
US20050131045A1 (en) * 2002-04-30 2005-06-16 Judith Aronhime Novel crystal forms of ondansetron, processes for their preparation, pharmaceutical, compositions containing the novel forms and methods for treating nausea using them
DE20320528U1 (en) * 2002-04-30 2004-09-16 Teva Pharmaceuticals Usa, Inc. New crystal forms of ondansetron and medicines that contain the new forms
FI6164U1 (en) * 2003-01-09 2004-03-15 Synthon Bv Ondansetronformer
US7390503B1 (en) 2003-08-22 2008-06-24 Barr Laboratories, Inc. Ondansetron orally disintegrating tablets
CN101014605A (en) * 2004-07-12 2007-08-08 卡地拉健康护理有限公司 Tricyclic pyrazole derivatives as cannabinoid receptor modulators
US7696356B2 (en) * 2004-08-17 2010-04-13 Taro Pharmaceutical Industries Limited Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one and ondansetron therefrom
WO2006046253A1 (en) * 2004-10-26 2006-05-04 Ipca Laboratories Limited A one-pot process for the preparation of antiemetic agent, 1,2,3,9-tetrahydro-9-methyl-3[(2-methyl)-1h-imidazole-1-yl)methyl]-4h-carbazol-4-o
CN115677561A (en) * 2022-11-01 2023-02-03 常州兰陵制药有限公司 1,2,3, 4-tetrahydro-9-methyl-4H-carbazolone and synthesis method thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3579534A (en) * 1969-05-09 1971-05-18 American Cyanamid Co Tetrahydrocarbazolecarboxylates
CN1011237B (en) * 1984-01-25 1991-01-16 格拉克索公司 Preparation of heterocyclic compounds
FI84349C (en) * 1984-01-25 1991-11-25 Glaxo Group Ltd PROCEDURE FOR THE FRAMEWORK OF PHARMACOLOGICAL PROPERTIES.
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
GB8617994D0 (en) * 1986-07-23 1986-08-28 Glaxo Group Ltd Heterocyclic compounds
GB8628473D0 (en) * 1986-11-28 1987-01-07 Glaxo Group Ltd Chemical compounds
JPH01258673A (en) * 1987-10-22 1989-10-16 Glaxo Group Ltd Ketone derivative

Also Published As

Publication number Publication date
KR940009152A (en) 1994-05-20
PL300685A1 (en) 1994-04-18
SI9300537B (en) 2003-02-28
ES2106936T5 (en) 2001-12-16
US5478949A (en) 1995-12-26
PL174526B1 (en) 1998-08-31
CA2106642C (en) 2005-08-16
DE69313771T2 (en) 1998-02-12
CN1052979C (en) 2000-05-31
HRP931292A2 (en) 1994-12-31
EP0595111B2 (en) 2001-08-16
UA27022C2 (en) 2000-02-28
EP0595111A1 (en) 1994-05-04
CN1089941A (en) 1994-07-27
ATE157973T1 (en) 1997-09-15
CN1235967A (en) 1999-11-24
PL174173B1 (en) 1998-06-30
GR3025599T3 (en) 1998-03-31
DK0595111T4 (en) 2001-10-22
DK0595111T3 (en) 1998-04-14
SK281243B6 (en) 2001-01-18
JP3378315B2 (en) 2003-02-17
CZ215693A3 (en) 1994-05-18
CN1083430C (en) 2002-04-24
RO115799B1 (en) 2000-06-30
EP0595111B1 (en) 1997-09-10
US5416221A (en) 1995-05-16
UA26893C2 (en) 1999-12-29
EE03071B1 (en) 1998-02-16
RU2119914C1 (en) 1998-10-10
DE69313771T3 (en) 2002-04-18
SI9300537A (en) 1994-06-30
DE69313771D1 (en) 1997-10-16
JPH06293734A (en) 1994-10-21
SK111093A3 (en) 1994-11-09
ES2106936T3 (en) 1997-11-16
HRP931292B1 (en) 1999-08-31
CZ284223B6 (en) 1998-09-16
KR100289912B1 (en) 2001-09-17

Similar Documents

Publication Publication Date Title
CA2264116A1 (en) Process for preparing intermediates to florfenicol
CA2106642A1 (en) Carbazolone derivatives and process for preparing the same
CA2105251A1 (en) Novel processes for the production of 13-ether derivatives of milbemycins, and novel intermediates therefor
CA2119261A1 (en) Novel sidechain-bearing taxanes and intermediates thereof
CA2634811A1 (en) Novel modifications to 2-amino-4-(4-fluorobenzylamino) -1- ethoxycarbonyl-aminobenzene and processes for preparing said compound
CA2172354A1 (en) Benzazepine-, benzoxazepine- and benzothiazepine-n-acetic acid derivatives, process for their preparation and pharmaceutical compositions containing them
CA2026143A1 (en) Triazole compounds, their production and use
CA2135039A1 (en) Solid-phase synthesis of oligoribonucleotides
EP0369691A3 (en) Process for preparing optically active 3-hydroxybutanoic acid
CA2188181A1 (en) Preparation of purines
CA2158130A1 (en) Process and Intermediates for Preparing Azabicyclo(2.2.2)Octan-3-Imines
CA2013518A1 (en) Derivatives of thieno-triazolo-diazepine, a preparation process of the same and therapeutic compositions containing them
CA2022653A1 (en) Dampening solution for lithographic printing
RU93049416A (en) DERIVATIVES OF CARBAZOLONA AND METHOD FOR THEIR PRODUCTION
CA2362217A1 (en) Process for preparing phenylpyrazole pesticidal intermediates
CA2281695A1 (en) Process for the preparation of substituted thiazolidinedione
CA2048896A1 (en) Fluoroethylcamptothecin derivatives
EP1116718A3 (en) Method for the preparation of taxol and its derivatives
CA2058888A1 (en) Phenoxyalkylcarboxylic acid derivatives and process of preparing the same
EP0688776A3 (en) Process for preparing silacyclo-hexane compounds
CA2059632A1 (en) Reveromycin a, method for preparing same, and antitumor agent and antifungal agent comprising the same
CA2124999A1 (en) Loracarbef isopropanolate and a process for converting loracarbef isopropanolate to loracarbef monohydrate
CA2022516A1 (en) Saccharide derivatives of protocatechualdehyde
CA2136597A1 (en) Hydrazine derivatives and uses thereof
CA2038011A1 (en) Processes for Preparing 2-Halogeno-3-Hydroxy-3-Phenyl-Propionic Acid Ester Compounds

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed