SI9300537B - Derivati karbazolona in postopek za njihovo pripravo - Google Patents
Derivati karbazolona in postopek za njihovo pripravo Download PDFInfo
- Publication number
- SI9300537B SI9300537B SI9300537A SI9300537A SI9300537B SI 9300537 B SI9300537 B SI 9300537B SI 9300537 A SI9300537 A SI 9300537A SI 9300537 A SI9300537 A SI 9300537A SI 9300537 B SI9300537 B SI 9300537B
- Authority
- SI
- Slovenia
- Prior art keywords
- formula
- group
- methyl
- compound
- variant
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 9
- 238000002360 preparation method Methods 0.000 title claims abstract 5
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- -1 2-methyl-1H-imidazol-1-yl group Chemical group 0.000 claims abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 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 claims abstract 2
- 229960005343 ondansetron Drugs 0.000 claims abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000010 aprotic solvent Substances 0.000 claims 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Photoreceptors In Electrophotography (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9203222A HU212934B (en) | 1992-10-14 | 1992-10-14 | Process for producing novel alkoxalylated carbazolone derivatives |
| HU9203223A HU212785B (en) | 1992-10-14 | 1992-10-14 | Process for producing of a carbazolone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9300537A SI9300537A (en) | 1994-06-30 |
| SI9300537B true SI9300537B (sl) | 2003-02-28 |
Family
ID=26318102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300537A SI9300537B (sl) | 1992-10-14 | 1993-10-13 | Derivati karbazolona in postopek za njihovo pripravo |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5416221A (cs) |
| EP (1) | EP0595111B2 (cs) |
| JP (1) | JP3378315B2 (cs) |
| KR (1) | KR100289912B1 (cs) |
| CN (2) | CN1052979C (cs) |
| AT (1) | ATE157973T1 (cs) |
| CA (1) | CA2106642C (cs) |
| CZ (1) | CZ284223B6 (cs) |
| DE (1) | DE69313771T3 (cs) |
| DK (1) | DK0595111T4 (cs) |
| EE (1) | EE03071B1 (cs) |
| ES (1) | ES2106936T5 (cs) |
| GR (1) | GR3025599T3 (cs) |
| HR (1) | HRP931292B1 (cs) |
| PL (2) | PL174526B1 (cs) |
| RO (1) | RO115799B1 (cs) |
| RU (1) | RU2119914C1 (cs) |
| SI (1) | SI9300537B (cs) |
| SK (1) | SK281243B6 (cs) |
| UA (2) | UA26893C2 (cs) |
Families Citing this family (16)
| 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 (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 |
| AU2002230935A1 (en) * | 2000-10-30 | 2002-05-15 | 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 |
| 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 |
| EP1499623B1 (en) * | 2002-04-29 | 2007-06-13 | TEVA Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-¬(2-methyl-1h-imidazol-1-yl)methyl|-4h-carbazol-4-one |
| KR20040104677A (ko) * | 2002-04-30 | 2004-12-10 | 비오갈 기오기스제르갸르 알티. | 신규의 온단세트론 결정 형태, 그 제조 방법, 그 신규의결정 형태를 함유하는 약학 조성물 및 이들을 이용한구역질 치료 방법 |
| 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 |
| FI6164U1 (fi) * | 2003-01-09 | 2004-03-15 | Synthon Bv | Ondansetronmuotoja |
| JP2007501284A (ja) * | 2003-06-10 | 2007-01-25 | スミスクライン ビーチャム コーポレーション | テトラヒドロカルバゾール誘導体およびそれらの薬学的使用 |
| US7390503B1 (en) | 2003-08-22 | 2008-06-24 | Barr Laboratories, Inc. | Ondansetron orally disintegrating tablets |
| GEP20094682B (en) * | 2004-07-12 | 2009-05-10 | Cadila Healthcare Ltd | 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 |
| CN101084190B (zh) * | 2004-12-27 | 2011-01-26 | 埃科特莱茵药品有限公司 | 作为crth2受体拮抗剂的2,3,4,9-四氢-1h-咔唑衍生物 |
| CN115677561B (zh) * | 2022-11-01 | 2024-04-05 | 常州兰陵制药有限公司 | 一种1,2,3,4-四氢-9-甲基-4h-咔唑酮及其合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3579534A (en) * | 1969-05-09 | 1971-05-18 | American Cyanamid Co | Tetrahydrocarbazolecarboxylates |
| PH22672A (en) * | 1984-01-25 | 1988-11-14 | Glaxo Group Ltd | Imidazolylmethyltetrahydrocarbazolone derivatives, composition and method of use thereof |
| CN1011237B (zh) * | 1984-01-25 | 1991-01-16 | 格拉克索公司 | 1，2，3，9-四氢-3-[(2-甲基-1h-咪唑-1-基)甲基]-4h-咔唑-4-酮类和其盐以及溶剂化物的制备 |
| 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 (ja) * | 1987-10-22 | 1989-10-16 | Glaxo Group Ltd | ケトン誘導体 |
-
1993
- 1993-09-21 CA CA002106642A patent/CA2106642C/en not_active Expired - Fee Related
- 1993-10-08 HR HR3223/92A patent/HRP931292B1/xx not_active IP Right Cessation
- 1993-10-11 UA UA93002172A patent/UA26893C2/uk unknown
- 1993-10-13 CN CN93119192A patent/CN1052979C/zh not_active Expired - Fee Related
- 1993-10-13 DE DE69313771T patent/DE69313771T3/de not_active Expired - Fee Related
- 1993-10-13 RO RO93-01370A patent/RO115799B1/ro unknown
- 1993-10-13 CZ CZ932156A patent/CZ284223B6/cs not_active IP Right Cessation
- 1993-10-13 SI SI9300537A patent/SI9300537B/sl not_active IP Right Cessation
- 1993-10-13 JP JP25588093A patent/JP3378315B2/ja not_active Expired - Fee Related
- 1993-10-13 KR KR1019930021223A patent/KR100289912B1/ko not_active Expired - Fee Related
- 1993-10-13 DK DK93116542T patent/DK0595111T4/da active
- 1993-10-13 RU RU93049416A patent/RU2119914C1/ru not_active IP Right Cessation
- 1993-10-13 ES ES93116542T patent/ES2106936T5/es not_active Expired - Lifetime
- 1993-10-13 SK SK1110-93A patent/SK281243B6/sk unknown
- 1993-10-13 AT AT93116542T patent/ATE157973T1/de not_active IP Right Cessation
- 1993-10-13 US US08/135,407 patent/US5416221A/en not_active Expired - Lifetime
- 1993-10-13 EP EP93116542A patent/EP0595111B2/en not_active Expired - Lifetime
- 1993-10-13 PL PL93324329A patent/PL174526B1/pl not_active IP Right Cessation
- 1993-10-13 PL PL93300685A patent/PL174173B1/pl not_active IP Right Cessation
-
1994
- 1994-07-19 EE EE9400092A patent/EE03071B1/xx 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/el unknown
-
1999
- 1999-05-11 CN CN99106445A patent/CN1083430C/zh not_active Expired - Fee Related
- 1999-05-24 UA UA99052847A patent/UA27022C2/uk unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the event date | ||
| KO00 | Lapse of patent |
Effective date: 20090603 |