CA2106642A1 - Carbazolone derivatives and process for preparing the same - Google Patents
Carbazolone derivatives and process for preparing the sameInfo
- 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
Links
- AMLYRCOEFHJSFS-UHFFFAOYSA-N carbazol-1-one Chemical class C1=CC=C2C3=CC=CC(=O)C3=NC2=C1 AMLYRCOEFHJSFS-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229960005343 ondansetron Drugs 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- -1 2-methyl-1H-imidazol-1-yl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; 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.
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.
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)
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)
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 |
-
1993
- 1993-09-21 CA CA002106642A patent/CA2106642C/en not_active Expired - Fee Related
- 1993-10-08 HR HR3223/92A patent/HRP931292B1/en not_active IP Right Cessation
- 1993-10-11 UA UA93002172A patent/UA26893C2/en unknown
- 1993-10-13 DK DK93116542T patent/DK0595111T4/en active
- 1993-10-13 AT AT93116542T patent/ATE157973T1/en not_active IP Right Cessation
- 1993-10-13 RU RU93049416A patent/RU2119914C1/en not_active IP Right Cessation
- 1993-10-13 PL PL93300685A patent/PL174173B1/en not_active IP Right Cessation
- 1993-10-13 CZ CZ932156A patent/CZ284223B6/en not_active IP Right Cessation
- 1993-10-13 CN CN93119192A patent/CN1052979C/en not_active Expired - Fee Related
- 1993-10-13 SI SI9300537A patent/SI9300537B/en not_active IP Right Cessation
- 1993-10-13 DE DE69313771T patent/DE69313771T3/en not_active Expired - Fee Related
- 1993-10-13 ES ES93116542T patent/ES2106936T5/en not_active Expired - Lifetime
- 1993-10-13 JP JP25588093A patent/JP3378315B2/en not_active Expired - Fee Related
- 1993-10-13 PL PL93324329A patent/PL174526B1/en not_active IP Right Cessation
- 1993-10-13 SK SK1110-93A patent/SK281243B6/en unknown
- 1993-10-13 EP EP93116542A patent/EP0595111B2/en not_active Expired - Lifetime
- 1993-10-13 KR KR1019930021223A patent/KR100289912B1/en not_active IP Right Cessation
- 1993-10-13 US US08/135,407 patent/US5416221A/en not_active Expired - Lifetime
- 1993-10-13 RO RO93-01370A patent/RO115799B1/en unknown
-
1994
- 1994-07-19 EE EE9400092A patent/EE03071B1/en not_active IP Right Cessation
- 1994-11-25 US US08/344,871 patent/US5478949A/en not_active Expired - Lifetime
-
1997
- 1997-12-04 GR GR970403244T patent/GR3025599T3/en unknown
-
1999
- 1999-05-11 CN CN99106445A patent/CN1083430C/en not_active Expired - Fee Related
- 1999-05-24 UA UA99052847A patent/UA27022C2/en unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |