DK169720B1 - Fluorerede 1-(alfa-phenylalkyl)-1H-1,2,3-triazolforbindelser samt deres fremstilling og farmaceutiske præparater indeholdende sådanne forbindelser - Google Patents
Fluorerede 1-(alfa-phenylalkyl)-1H-1,2,3-triazolforbindelser samt deres fremstilling og farmaceutiske præparater indeholdende sådanne forbindelser Download PDFInfo
- Publication number
- DK169720B1 DK169720B1 DK175686A DK175686A DK169720B1 DK 169720 B1 DK169720 B1 DK 169720B1 DK 175686 A DK175686 A DK 175686A DK 175686 A DK175686 A DK 175686A DK 169720 B1 DK169720 B1 DK 169720B1
- Authority
- DK
- Denmark
- Prior art keywords
- triazole
- carbamyl
- formula
- carboxamide
- difluorobenzyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 76
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- -1 2,6-difluorophenyl Chemical group 0.000 claims description 67
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
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- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical group N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 claims description 3
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- REQQDJGYRQVUEY-UHFFFAOYSA-N 1-[(2,5-difluorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=CC(F)=CC=C1F REQQDJGYRQVUEY-UHFFFAOYSA-N 0.000 claims description 2
- YGJSCFVQYUIZMC-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]triazole-4-carboxamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1Cl YGJSCFVQYUIZMC-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000006287 difluorobenzyl group Chemical group 0.000 claims 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- MJXUZAHRGOEWSQ-UHFFFAOYSA-N trimethyl(triazol-1-yl)silane Chemical class C[Si](C)(C)N1C=CN=N1 MJXUZAHRGOEWSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH166385 | 1985-04-18 | ||
| CH166385 | 1985-04-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK175686D0 DK175686D0 (da) | 1986-04-17 |
| DK175686A DK175686A (da) | 1986-10-19 |
| DK169720B1 true DK169720B1 (da) | 1995-01-23 |
Family
ID=4215715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK175686A DK169720B1 (da) | 1985-04-18 | 1986-04-17 | Fluorerede 1-(alfa-phenylalkyl)-1H-1,2,3-triazolforbindelser samt deres fremstilling og farmaceutiske præparater indeholdende sådanne forbindelser |
Country Status (22)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3578499D1 (de) * | 1984-02-02 | 1990-08-09 | Merck & Co Inc | 5-(amino oder substituiertes amino)-1,2,3-triazole. |
| WO1997040025A1 (en) * | 1996-04-19 | 1997-10-30 | Novo Nordisk A/S | Solid phase and combinatorial synthesis of substituted 1,2,3-triazoles and of arrays of substituted 1,2,3-triazoles |
| SK283990B6 (sk) * | 1996-07-11 | 2004-07-07 | Novartis Ag | Spôsob prípravy 1-substituovaných 4-kyano-1,2,3-triazolov, 4-kyano-1-(2,6-difluórbenzyl)-1H-1,2,3-triazol |
| TW403740B (en) * | 1997-06-10 | 2000-09-01 | Novartis Ag | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
| TW513301B (en) * | 1999-03-01 | 2002-12-11 | Novartis Ag | Pharmaceutical composition for treatment of neuropathic pain and affective and attention disorders |
| WO2004106329A2 (en) * | 2003-06-03 | 2004-12-09 | Dr. Reddy's Laboratories Ltd. | Novel antiinfective compounds and their pharmaceutical compositions |
| IT1393368B1 (it) * | 2009-03-23 | 2012-04-20 | Dipharma Francis Srl | Metodo per la preparazione di rufinamide |
| IT1395736B1 (it) | 2009-08-04 | 2012-10-19 | Dipharma Francis Srl | Forme cristalline di rufinamide |
| JP2013525413A (ja) * | 2010-04-30 | 2013-06-20 | ラボラトリオス レスヴィ，エス．エル． | ルフィナマイド中間体の改良された製造方法 |
| ITMI20110718A1 (it) | 2011-04-29 | 2012-10-30 | Dipharma Francis Srl | Procedimento per la purificazione di rufinamide |
| US20150368211A1 (en) * | 2013-01-31 | 2015-12-24 | The Johns Hopkins University | Rufinamide and derivatives and their use in modulating the gating process of human voltage-gated sodium channels |
| US9771335B2 (en) * | 2015-07-31 | 2017-09-26 | The Johns Hopkins University | Derivatives of rufinamide and their use in inhibtion of the activation of human voltage-gated sodium channels |
| ES2902685T3 (es) | 2015-12-11 | 2022-03-29 | Univ Aarhus | Rufinamida para uso en el tratamiento de la miotonía |
| WO2021099481A1 (en) | 2019-11-20 | 2021-05-27 | Medichem, S.A. | Solid composition containing rufinamide |
| CN116874438A (zh) * | 2023-06-02 | 2023-10-13 | 大连理工大学 | 一锅法制备多取代1,2,3-三唑类化合物 |
| CN116854644A (zh) * | 2023-07-06 | 2023-10-10 | 浙江大学 | 5-氨基-1-烷基-1h-1,2,3-三氮唑-4-甲酰胺类化合物及其制备和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1511195A (en) * | 1976-10-18 | 1978-05-17 | Ici America Inc | Triazole derivatives |
| FI834666A7 (fi) * | 1982-12-23 | 1984-06-24 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya aralkyltriazolfoereningar. |
-
1986
- 1986-04-14 PH PH33651A patent/PH22568A/en unknown
- 1986-04-14 FI FI861573A patent/FI93544C/fi not_active IP Right Cessation
- 1986-04-15 EP EP86105188A patent/EP0199262B1/de not_active Expired - Lifetime
- 1986-04-15 DE DE8686105188T patent/DE3677626D1/de not_active Expired - Lifetime
- 1986-04-15 IL IL78510A patent/IL78510A/xx not_active IP Right Cessation
- 1986-04-16 GR GR861004A patent/GR861004B/el unknown
- 1986-04-16 PT PT82400A patent/PT82400B/pt unknown
- 1986-04-16 CA CA000506774A patent/CA1272201A/en not_active Expired - Lifetime
- 1986-04-16 DD DD86289243A patent/DD245874A5/de not_active IP Right Cessation
- 1986-04-16 ES ES554024A patent/ES8800176A1/es not_active Expired
- 1986-04-16 NO NO861486A patent/NO164295C/no unknown
- 1986-04-17 DK DK175686A patent/DK169720B1/da not_active IP Right Cessation
- 1986-04-17 IE IE101586A patent/IE58472B1/en not_active IP Right Cessation
- 1986-04-17 HU HU861615A patent/HU203327B/hu unknown
- 1986-04-17 NZ NZ215871A patent/NZ215871A/xx unknown
- 1986-04-17 ZA ZA862873A patent/ZA862873B/xx unknown
- 1986-04-17 AU AU56319/86A patent/AU599024B2/en not_active Expired
- 1986-04-17 KR KR1019860002954A patent/KR900008810B1/ko not_active Expired
- 1986-04-18 JP JP61088384A patent/JPS61243068A/ja active Granted
-
1987
- 1987-07-31 ES ES557641A patent/ES8802501A1/es not_active Expired
-
1992
- 1992-06-26 MX MX9203628A patent/MX9203628A/es unknown
-
1994
- 1994-01-06 HK HK14/94A patent/HK1494A/xx not_active IP Right Cessation
- 1994-06-03 CY CY175194A patent/CY1751A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| AHB | Application shelved due to non-payment | ||
| PUP | Patent expired |