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
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- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Otolaryngology (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)
Claims (6)
- -1 - Derivati karbazolona in postopek za njihovo pripravo PATENTNI ZAHTEVKI 1. Nove spojine s formulo 0v kateri A stoji za skupino s formulo - CH2 -R (V) v kateri R pomeni 2-metil-lH-imidazol-l-ilno skupino, B predstavlja skupino s formulo 0 (VI) II -C-C00R1 v kateri R^ pomeni vodik ali A in B skupaj tvorita skupino s formulo OH coor2 skupino; ali v kateri R2 pomeni metilno (VII), (VIII) -ζ- Α in Β skupaj tvorita skupino s formuloC 0il 0
- 2. Spojina, označena s tem, da je izbrana iz skupine 3-ctoksioksalί 1 -9-meti 1-1,2,3,9-letrahidro-4I l-karbazol-4-on. lakton 3-hidroksimetil-9-metil-l,2,3,9-tetrahidro-4H-karbazol-4-on-3-glioksilne kisline in 9-metil-3-[(2-metil-lH-imidazol-l-il)metil]-l,2,3,9-tetrahidro-4H-karbazol-4-on-3-glioksilna kislina.
- 3. Nov postopek za pripravo spojin s formulo 0(I) v kateri A stoji za skupino s formulo ch2 -r (V) v kateri R pomeni 2-metil-lH-imidazol-l-ilno skupino B predstavlja skupino s formulo 0 II — C —COOR-j (VI) - 3- v kateri Rj[ pomeni vodik ali A in B skupaj tvorita skupino s formulo OH (VII) coor2 v kateri R2 pomeni etilno skupino; ali A in B skupaj tvorita skupino s formulo označen s tem, da a) keton s formulo(VIII) (III) reagira z di(Cp2 alkil)oksalatom v prisotnosti bazičnega sredstva, da dobimo novo spojino s formulo(la) kjer R.2 stoji za etilno skupino; b) spojina s formulo (la), kjer ima R2 pri stopnji a) zgoraj navedeni pomen, reagira s formaldehidom v prisotnosti bazičnega katalizatorja v aprotičnem topilu, da dobimo novo spojino s formulo (Ic) 0(Ic) c) spojina s formulo (Ic) reagira z 2-metilimidazolom s formulo (IV). da dobimo novo spojino s formulo (Id)(Id) d) spojina s formulo (Id) reagira z bazo. prednostno karbonatom ali hidroksidom alkalijske kovine, da dobimo ondansetron s formulo (II). (II) -s -in po želji pretvorimo ondanseliOn s formulo (U) v njegovo farmacevtsko sprejemljivo kislinsko adacijsko sol.
- 4. Postopek po zahtevku 3, varianta b), označen s tem, da obsega izvedbo reakcije spojine s formulo (la), kjer ima R2 zgoraj definirani pomen, s formaldehidom ob uporabi 1 do 2 molov, prednostno 1.2 do 1.6 molov formaldehida v prisotnosti ne več kot 0.2 molov bazičnega katalizatorja, prednostno karbonata alkalijske kovine ali trialkilamina. 1 b.
- Postopek po zahtevku 3, varianta b), za pripravo spojine s formulo (Ic), označen s tem, da izvedemo reakcijo s formaldehidom v dipolarnem aprotičnem topilu.
- 6. Postopek po zahtevku 3, varianta c), označen s tem. da uporabimo 2-metilimiduzol v množini 1.0 do 3.0 molov, računano na spojino s formulo (le). J. Postopek po zahtevku 3, varianta d), označen s tem, da odcepimo oksalilno skupino z alkoholizo vezi C-C v prisotnosti Cj^alkanola in vežemo skupino, odstranjeno pri tvorbi soli, z bazo močnejšo od 2-metilimidazola, prednostno s trietilaminom. S. Postopek po kateremkoli izmed zahtevkov 3, varianta c), ali zahtevku 7 ali zahtevku 8, označen s tem, da uporabimo kot topilo aprotično topilo, prednostno topilo etrskega tipa ali dimetilsulfoksid, sulfolan ali dimetilformamid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9203223A HU212785B (en) | 1992-10-14 | 1992-10-14 | Process for producing of a carbazolone derivative |
| HU9203222A HU212934B (en) | 1992-10-14 | 1992-10-14 | Process for producing novel alkoxalylated carbazolone derivatives |
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 (sl) |
| EP (1) | EP0595111B2 (sl) |
| JP (1) | JP3378315B2 (sl) |
| KR (1) | KR100289912B1 (sl) |
| CN (2) | CN1052979C (sl) |
| AT (1) | ATE157973T1 (sl) |
| CA (1) | CA2106642C (sl) |
| CZ (1) | CZ284223B6 (sl) |
| DE (1) | DE69313771T3 (sl) |
| DK (1) | DK0595111T4 (sl) |
| EE (1) | EE03071B1 (sl) |
| ES (1) | ES2106936T5 (sl) |
| GR (1) | GR3025599T3 (sl) |
| HR (1) | HRP931292B1 (sl) |
| PL (2) | PL174173B1 (sl) |
| RO (1) | RO115799B1 (sl) |
| RU (1) | RU2119914C1 (sl) |
| SI (1) | SI9300537B (sl) |
| SK (1) | SK281243B6 (sl) |
| UA (2) | UA26893C2 (sl) |
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 (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 |
| KR20030042038A (ko) * | 2000-10-30 | 2003-05-27 | 테바 파마슈티컬 인더스트리즈 리미티드 | 온단세트론 히드로클로라이드의 신규한 결정 형태 및용매화물 형태와 이들의 제조 방법 |
| 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 |
| JP2005529142A (ja) * | 2002-04-29 | 2005-09-29 | テバ ジョジセルジャール レースベニュタールシャシャーグ | １，２，３，９−テトラヒドロ−９−メチル−３−［（２−メチル−１ｈ−イミダゾル−１−イル）メチル］−４ｈ−カルバゾル−４−オンの製造方法 |
| JP2005529908A (ja) * | 2002-04-30 | 2005-10-06 | テバ ジョジセルジャール レースベニュタールシャシャーグ | オンダンセトロンの新規結晶形、その製法、当該新規形を含有する医薬組成物、及び当該組成物を用いる吐気の治療方法 |
| 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 |
| US7390503B1 (en) | 2003-08-22 | 2008-06-24 | Barr Laboratories, Inc. | Ondansetron orally disintegrating tablets |
| US8030345B2 (en) * | 2004-07-12 | 2011-10-04 | Cadila Healthcare Limited | 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 |
| US7547791B2 (en) * | 2004-10-26 | 2009-06-16 | Ipca Laboratories Ltd. | 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 |
| 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 |
| 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 |
| PT79890B (en) * | 1984-01-25 | 1987-02-03 | Glaxo Group Ltd | Process for preparing tetrahydro-methylimidazolylcarbazolones |
| 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 |
| 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 |
| US4939144A (en) * | 1987-10-22 | 1990-07-03 | Glaxo Group Limited | Tricyclic ketone derivatives as 5-HT antagonists |
-
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 KR KR1019930021223A patent/KR100289912B1/ko not_active IP Right Cessation
- 1993-10-13 DK DK93116542T patent/DK0595111T4/da active
- 1993-10-13 EP EP93116542A patent/EP0595111B2/en not_active Expired - Lifetime
- 1993-10-13 SI SI9300537A patent/SI9300537B/sl not_active IP Right Cessation
- 1993-10-13 RU RU93049416A patent/RU2119914C1/ru not_active IP Right Cessation
- 1993-10-13 SK SK1110-93A patent/SK281243B6/sk unknown
- 1993-10-13 PL PL93300685A patent/PL174173B1/pl not_active IP Right Cessation
- 1993-10-13 PL PL93324329A patent/PL174526B1/pl not_active IP Right Cessation
- 1993-10-13 ES ES93116542T patent/ES2106936T5/es not_active Expired - Lifetime
- 1993-10-13 CN CN93119192A patent/CN1052979C/zh not_active Expired - Fee Related
- 1993-10-13 RO RO93-01370A patent/RO115799B1/ro unknown
- 1993-10-13 US US08/135,407 patent/US5416221A/en not_active Expired - Lifetime
- 1993-10-13 CZ CZ932156A patent/CZ284223B6/cs not_active IP Right Cessation
- 1993-10-13 JP JP25588093A patent/JP3378315B2/ja not_active Expired - Fee Related
- 1993-10-13 DE DE69313771T patent/DE69313771T3/de not_active Expired - Fee Related
- 1993-10-13 AT AT93116542T patent/ATE157973T1/de 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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| IF | Valid on the event date | ||
| KO00 | Lapse of patent |
Effective date: 20090603 |