BG60427B2 - 1,2,4-триазинови производни, метод за получаването им и фармацевтични състави съдържащи ги - Google Patents
1,2,4-триазинови производни, метод за получаването им и фармацевтични състави съдържащи ги Download PDFInfo
- Publication number
- BG60427B2 BG60427B2 BG097992A BG9799293A BG60427B2 BG 60427 B2 BG60427 B2 BG 60427B2 BG 097992 A BG097992 A BG 097992A BG 9799293 A BG9799293 A BG 9799293A BG 60427 B2 BG60427 B2 BG 60427B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- formula
- hydrogen
- compound
- iii
- triazine
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000000034 method Methods 0.000 title abstract description 6
- 150000003919 1,2,3-triazines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 206010015037 epilepsy Diseases 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
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- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
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- 239000011737 fluorine Substances 0.000 claims description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
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- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
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- 239000003906 humectant Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940080428 lactose 200 mg Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960000901 mepacrine Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FGAVGUMJSPGHSU-UHFFFAOYSA-N n'-[3-amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-5-yl]-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl FGAVGUMJSPGHSU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
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- GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7919257 | 1979-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60427B2 true BG60427B2 (bg) | 1995-03-31 |
Family
ID=10505597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG097992A BG60427B2 (bg) | 1979-06-01 | 1993-07-29 | 1,2,4-триазинови производни, метод за получаването им и фармацевтични състави съдържащи ги |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US4486354A (sv) |
| EP (2) | EP0059987B1 (sv) |
| JP (2) | JPS5625169A (sv) |
| AR (1) | AR227521A1 (sv) |
| AT (1) | AT370097B (sv) |
| AU (2) | AU530999B2 (sv) |
| BG (1) | BG60427B2 (sv) |
| CA (1) | CA1112643A (sv) |
| CS (1) | CS234018B2 (sv) |
| CZ (1) | CZ384891A3 (sv) |
| DD (1) | DD151309A5 (sv) |
| DK (1) | DK153787C (sv) |
| ES (1) | ES8104993A1 (sv) |
| FI (1) | FI67844C (sv) |
| GE (1) | GEP19960470B (sv) |
| GR (1) | GR68380B (sv) |
| HU (1) | HU182086B (sv) |
| IE (1) | IE49823B1 (sv) |
| IL (1) | IL60201A (sv) |
| IT (1) | IT1147087B (sv) |
| MX (1) | MX9202962A (sv) |
| MY (1) | MY8500062A (sv) |
| NL (1) | NL950007I2 (sv) |
| NZ (1) | NZ193890A (sv) |
| PL (1) | PL124029B1 (sv) |
| SU (1) | SU1055331A3 (sv) |
| UA (1) | UA5576A1 (sv) |
| YU (1) | YU145680A (sv) |
| ZA (1) | ZA803250B (sv) |
| ZW (1) | ZW12980A1 (sv) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0086502B1 (en) * | 1979-08-16 | 1987-03-25 | The Wellcome Foundation Limited | Substituted aromatic triazines |
| GB8328757D0 (en) * | 1983-10-27 | 1983-11-30 | Wellcome Found | Chemical compounds |
| DE3600891A1 (de) * | 1986-01-15 | 1987-07-16 | Bayer Ag | 1,8-verbrueckte 4-chinolon-3-carbonsaeuren und diese enthaltende arzneimittel |
| GB8613183D0 (en) * | 1986-05-30 | 1986-07-02 | Wellcome Found | Triazine salt |
| US4972496A (en) * | 1986-07-25 | 1990-11-20 | Grid Systems Corporation | Handwritten keyboardless entry computer system |
| FI895821A0 (fi) * | 1988-12-07 | 1989-12-05 | Wellcome Found | Farmaceutiskt aktiva cns foereningar. |
| US5136080A (en) * | 1989-12-04 | 1992-08-04 | Burroughs Wellcome Co. | Nitrile compounds |
| GB9012311D0 (en) * | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns compounds |
| GB9012312D0 (en) * | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns compounds |
| GB2257363B (en) * | 1991-01-30 | 1994-09-28 | Wellcome Found | Water dispersible tablets containing acyclovir |
| GB9124807D0 (en) * | 1991-11-22 | 1992-01-15 | Wellcome Found | Pharmaceutical formulations |
| US5629016A (en) * | 1991-01-30 | 1997-05-13 | Glaxo Wellcome Inc. | Water-dispersible tablets |
| GB9203483D0 (en) * | 1992-02-19 | 1992-04-08 | Wellcome Found | Anti-inflammatory compounds |
| WO1993025207A1 (en) * | 1992-06-12 | 1993-12-23 | The Wellcome Foundation Limited | Use of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine isethionate for the treatment and prevention of dependence, tolerance and sensitization of drugs |
| GB9215908D0 (en) * | 1992-07-27 | 1992-09-09 | Wellcome Found | Water dispersible tablets |
| FR2699077B1 (fr) * | 1992-12-16 | 1995-01-13 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants dans le traitement de lésions neurologiques liées à des traumatismes. |
| US6133299A (en) * | 1993-02-25 | 2000-10-17 | Warner-Lambert Company | Methods for treating neurodegenerative diseases and disorders using N-(2,6-disubstituted aromatic)-N'-pyridinyl ureas and other anticonvulsant compounds |
| US5866597A (en) * | 1993-03-19 | 1999-02-02 | Glaxo Wellcome Inc. | Use of triazine compounds for the treatment of memory and learning disorders |
| GB9305693D0 (en) * | 1993-03-19 | 1993-05-05 | Wellcome Found | Therapeutic triazine compounds and use |
| GB9305692D0 (en) * | 1993-03-19 | 1993-05-05 | Wellcome Found | Therapeutic triazine compounds and use |
| US5698226A (en) * | 1993-07-13 | 1997-12-16 | Glaxo Wellcome Inc. | Water-dispersible tablets |
| GB9317146D0 (en) * | 1993-08-18 | 1993-10-06 | Wellcome Found | Therapeutic combinations |
| GB9424766D0 (en) * | 1994-12-07 | 1995-02-08 | Wellcome Found | Pharmaceutical composition |
| WO1996020934A1 (en) * | 1994-12-30 | 1996-07-11 | The Wellcome Foundation Limited | Process for the preparation of lamotrigine |
| GB9426448D0 (en) * | 1994-12-30 | 1995-03-01 | Wellcome Found | Process |
| GB9512854D0 (en) * | 1995-06-23 | 1995-08-23 | Wellcome Found | Novel formulation |
| GB9518027D0 (en) * | 1995-09-05 | 1995-11-08 | Wellcome Found | Pharmacologically active compound |
| FR2741879A1 (fr) * | 1995-12-05 | 1997-06-06 | Esteve Labor Dr | Derives de fluorophenyl-triazines et pyrimidines, leur preparation et leur application en tant que medicament |
| US6202491B1 (en) | 1997-07-22 | 2001-03-20 | Skf Condition Monitoring, Inc. | Digital vibration coupling stud |
| GB9726987D0 (en) * | 1997-12-22 | 1998-02-18 | Glaxo Group Ltd | Compounds |
| US6124500A (en) * | 1998-03-09 | 2000-09-26 | Rohm And Haas Company | Process for synthesizing benzoic acids |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| CA2334937C (en) * | 1998-12-14 | 2004-09-21 | Torrent Pharmaceuticals Ltd. | An improved process for the preparation of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine |
| US20020055177A1 (en) * | 1999-03-10 | 2002-05-09 | Glaxo Wellcome Inc. | Compound and its use |
| GB9907965D0 (en) * | 1999-04-09 | 1999-06-02 | Glaxo Group Ltd | Medical use |
| EP1169060B1 (en) * | 1999-04-09 | 2005-08-31 | Euro-Celtique S.A. | Sodium channel blocker compositions and the use thereof |
| AU763244B2 (en) * | 2000-01-03 | 2003-07-17 | Rpg Life Sciences Limited | A process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine |
| IL134730A (en) * | 2000-02-25 | 2003-10-31 | Chemagis Ltd | Process for preparing substituted benzoyl cyanide amidinohydrazones |
| PL365378A1 (en) | 2000-11-30 | 2005-01-10 | Pfizer Products Inc. | Combination of gaba agonists and aldose reductase inhibitors |
| PT1337271E (pt) | 2000-11-30 | 2005-01-31 | Pfizer Prod Inc | Combinacao de agonistas de gaba e inibidores de sorbitol desidrogenase |
| WO2002068398A1 (en) * | 2001-02-27 | 2002-09-06 | Teva Pharmaceutical Industries Ltd. | New crystal forms of lamotrigine and processes for their preparations |
| PT1423168E (pt) * | 2001-09-03 | 2006-05-31 | Newron Pharm Spa | Composicao farmaceutica que compreende gabapentina ou um seu analogo e uma x-aminoamida e a sua utilizacao como analgesico |
| CA2366521C (en) | 2001-12-24 | 2007-03-06 | Brantford Chemicals Inc. | A new and efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines |
| IL163666A0 (en) | 2002-02-22 | 2005-12-18 | New River Pharmaceuticals Inc | Active agent delivery systems and methods for protecting and administering active agents |
| WO2003090693A2 (en) * | 2002-04-23 | 2003-11-06 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing lamotrigine particles of defined morphology |
| US8637512B2 (en) | 2002-07-29 | 2014-01-28 | Glaxo Group Limited | Formulations and method of treatment |
| HU225667B1 (en) | 2002-09-20 | 2007-05-29 | Richter Gedeon Nyrt | Method for producing high-purity 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine |
| ES2209639B1 (es) | 2002-10-31 | 2005-08-01 | Vita Cientifica, S.L. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y obtencion de su intermedio. |
| EP1603889A1 (en) * | 2003-03-17 | 2005-12-14 | Hetero Drugs Limited | Novel crystalline forms of lamotrigine |
| US7504516B2 (en) | 2003-03-27 | 2009-03-17 | Hetero Drugs Limited | Crystalline forms of candesartan cilexetil |
| MXPA05012317A (es) | 2003-05-16 | 2006-01-30 | Pfizer Prod Inc | Combinaciones terapeuticas de agentes antipsicoticos atipicos con agentes moduladores del gaba anticonvulsivos o benzodiazepinas. |
| WO2004103340A1 (en) * | 2003-05-20 | 2004-12-02 | Ranbaxy Laboratories Limited | Water dispersible tablets of lamotrigine |
| GB2395483A (en) * | 2003-07-03 | 2004-05-26 | Jubilant Organosys Ltd | Crystalline lamotrigine and its monohydrate |
| EP1691811B1 (en) | 2003-12-11 | 2014-07-23 | Sunovion Pharmaceuticals Inc. | Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression |
| JP2007537151A (ja) * | 2004-01-29 | 2007-12-20 | ファイザー・プロダクツ・インク | γ−アミノ酪酸モジュレータと５−ＨＴ１Ｂ受容体アンタゴニストとの組合せ |
| EP1737473A4 (en) * | 2004-04-19 | 2009-08-26 | Noven Therapeutics Llc | COMBINATIONS OF LITHIUM AND USES THEREOF |
| KR101277520B1 (ko) * | 2004-09-10 | 2013-06-21 | 뉴론 파마슈티칼즈 에스. 피. 에이. | （할로벤질옥시）벤질아미노－프로판아미드를 포함하는 선택적 나트륨 및／또는 칼슘 채널 조절제로서 유용한 약제학적 조성물 |
| US7825151B2 (en) * | 2005-09-23 | 2010-11-02 | Janssen Pharmaceutica Nv | Hexahydro-cyclooctyl pyrazole cannabinoid modulators |
| US20070123578A1 (en) * | 2005-09-23 | 2007-05-31 | Fina Liotta | Hexahydro-cycloheptapyrazole cannabinoid modulators |
| US8378117B2 (en) * | 2005-09-23 | 2013-02-19 | Janssen Pharmaceutica N.V. | Hexahydro-cycloheptapyrazole cannabinoid modulators |
| US8378096B2 (en) * | 2005-09-23 | 2013-02-19 | Janssen Pharmaceutica N.V. | Hexahydro-cycloheptapyrazole cannabinoid modulators |
| BRPI0616263A2 (pt) | 2005-09-23 | 2011-06-14 | Janssen Pharmaceutica Nv | moduladores canabinàides do tipo tetrahidro-ciclopentil pirazol |
| UA93389C2 (en) * | 2005-09-23 | 2011-02-10 | Янссен Фармацевтика H.B. | Hexahydro cyclooctyl pyrazole cannabinoid modulators |
| US20070117858A1 (en) * | 2005-11-23 | 2007-05-24 | Mingde Xia | Substituted 5-heteroaryl-1-phenyl-pyrazole cannabinoid modulators |
| US7526911B2 (en) * | 2006-02-03 | 2009-05-05 | Rolls-Royce Corporation | Gas turbine engine fuel system with fuel metering valve |
| US7795294B2 (en) * | 2006-02-14 | 2010-09-14 | Janssen Pharmaceutica N.V. | Tetrahydro-2H-indazole pyrazole cannabinoid modulators |
| US8012957B2 (en) * | 2006-03-27 | 2011-09-06 | Janssen Pharmaceutica Nv | Tetrahydro-1H-1,2,6-triaza-azulene cannabinoid modulators |
| US20070254911A1 (en) * | 2006-03-27 | 2007-11-01 | Mingde Xia | Tetrahydro-Pyrazolo[3,4-c]Pyridine Cannabinoid Modulators |
| WO2007122638A2 (en) * | 2006-04-26 | 2007-11-01 | Ratnamani Bio-Chemicals & Pharmaceuticals Pvt. Ltd. | An improved process for preparation of lamotrigine intermediates |
| ES2337415T3 (es) * | 2006-05-31 | 2010-04-23 | Calaire Chimie Sas | Metodo para la preparacion de lamotrigina y su producto intermedio cloruro de 2,3-diclorobenzoilo. |
| GB0613836D0 (en) * | 2006-07-13 | 2006-08-23 | Univ Greenwich | New medical use of triazine derivatives |
| US20120142919A1 (en) | 2006-08-02 | 2012-06-07 | Medichem, S.A. | Method for synthesizing lamotrigine |
| CA2659290A1 (en) * | 2006-08-14 | 2008-02-21 | Jean-Paul Roduit | A process for the preparation of lamotrigine |
| EP2117538A1 (en) | 2007-01-24 | 2009-11-18 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5- (5-trifluoromethyl-tetrazol-i-yl-benzyl) - (2s-phenyl-piperidin-3s-yl-) |
| US7943653B2 (en) * | 2007-08-13 | 2011-05-17 | Janssen Pharmaceutica N.V. | Substituted 5-vinylphenyl-1-phenyl-pyrazole cannabinoid modulators |
| US20090076010A1 (en) * | 2007-09-13 | 2009-03-19 | Protia, Llc | Deuterium-enriched lamotrigine |
| US8486927B2 (en) * | 2007-11-09 | 2013-07-16 | Thar Pharmaceuticals | Crystalline forms of lamotrigine |
| GB0800741D0 (en) | 2008-01-16 | 2008-02-20 | Univ Greenwich | Cyclic triazo and diazo sodium channel blockers |
| US20100190752A1 (en) | 2008-09-05 | 2010-07-29 | Gruenenthal Gmbh | Pharmaceutical Combination |
| MX2011012044A (es) | 2009-05-13 | 2011-12-14 | Nektar Therapeutics | Compuestos de triazina aromatica sustituida que contienen oligomeros. |
| EP2564836A1 (en) | 2009-05-20 | 2013-03-06 | Ranbaxy Laboratories Limited | Controlled release lamotrigine formulations |
| GB2471713A (en) | 2009-07-08 | 2011-01-12 | Univ Greenwich | 1,2,4-triazine derivatives and their use as sodium channel blockers |
| GB2471729A (en) | 2009-07-08 | 2011-01-12 | Univ Greenwich | 1,2,4-triazine derivatives and their use as sodium channel blockers |
| US20110052686A1 (en) | 2009-09-03 | 2011-03-03 | Ranbaxy Laboratories Limited | Modified release lamotrigine tablets |
| GB201111712D0 (en) | 2011-07-08 | 2011-08-24 | Gosforth Ct Holdings Pty Ltd | Pharmaceutical compositions |
| WO2013183985A1 (en) | 2012-06-05 | 2013-12-12 | Erasmus University Medical Center Rotterdam | Method of treating cognitive impairment and compounds for use therein |
| US10189859B2 (en) | 2013-12-21 | 2019-01-29 | Nektar Therapeutics | Derivatives of 6-(2,3-dichlorophenyl)-1,2,4-triazin-5-amine |
| US10576086B2 (en) | 2015-06-12 | 2020-03-03 | University Of Greenwich | Triazine derivatives as interferon-gamma inhibitors |
| TWI808952B (zh) | 2016-12-16 | 2023-07-21 | 瑞士商愛杜西亞製藥有限公司 | 包含t型鈣通道阻斷劑之醫藥組合 |
| TWI826531B (zh) | 2018-09-21 | 2023-12-21 | 南韓商愛思開生物製藥股份有限公司 | 具有㗁二唑之化合物及包含該化合物之醫藥組合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB759014A (en) * | 1952-02-26 | 1956-10-10 | Wellcome Found | Improvements in triazines and their manufacture |
| AT190941B (de) * | 1954-09-22 | 1957-07-25 | Chemie Linz Ag | Verfahren zur Herstellung neuer Guanylhydrazone |
| US2952677A (en) * | 1956-10-01 | 1960-09-13 | Ici Ltd | Aminoguanadine compounds |
| BE663481A (sv) * | 1964-05-05 | |||
| DE1802364C3 (de) * | 1967-10-12 | 1975-03-20 | Shell Internationale Research Maatschappij B.V., Den Haag (Niederlande) | Arzneimittel mit thymeretischer Wirkung |
| GB1223491A (en) * | 1967-10-13 | 1971-02-24 | American Home Prod | Guanidines |
| US3637688A (en) * | 1970-01-09 | 1972-01-25 | American Home Prod | 6-(fluoro and trifluoromethyl phenyl)-3 5-diamino - 1 2 4 - triazines and substituted - 6 - phenylalkyl-3,5-diamino-1 2 4-triazines |
| EP0086502B1 (en) * | 1979-08-16 | 1987-03-25 | The Wellcome Foundation Limited | Substituted aromatic triazines |
-
1980
- 1980-05-30 DK DK233880A patent/DK153787C/da active
- 1980-05-30 NZ NZ193890A patent/NZ193890A/en unknown
- 1980-05-30 AT AT0289680A patent/AT370097B/de not_active IP Right Cessation
- 1980-05-30 AU AU58906/80A patent/AU530999B2/en not_active Expired
- 1980-05-30 ES ES491998A patent/ES8104993A1/es not_active Expired
- 1980-05-30 HU HU801364A patent/HU182086B/hu unknown
- 1980-05-30 AR AR281263A patent/AR227521A1/es active
- 1980-05-30 EP EP82102293A patent/EP0059987B1/en not_active Expired
- 1980-05-30 FI FI801758A patent/FI67844C/fi not_active IP Right Cessation
- 1980-05-30 IE IE1126/80A patent/IE49823B1/en not_active IP Right Cessation
- 1980-05-30 JP JP7158080A patent/JPS5625169A/ja active Granted
- 1980-05-30 CA CA353,081A patent/CA1112643A/en not_active Expired
- 1980-05-30 ZW ZW129/80A patent/ZW12980A1/xx unknown
- 1980-05-30 CS CS803829A patent/CS234018B2/cs unknown
- 1980-05-30 IL IL60201A patent/IL60201A/xx unknown
- 1980-05-30 EP EP80103032A patent/EP0021121B1/en not_active Expired
- 1980-05-30 IT IT48848/80A patent/IT1147087B/it active Protection Beyond IP Right Term
- 1980-05-30 GR GR62081A patent/GR68380B/el unknown
- 1980-05-30 DD DD80221474A patent/DD151309A5/de unknown
- 1980-05-30 PL PL1980224633A patent/PL124029B1/pl unknown
- 1980-05-30 ZA ZA00803250A patent/ZA803250B/xx unknown
- 1980-05-31 YU YU01456/80A patent/YU145680A/xx unknown
- 1980-06-02 UA UA2932704A patent/UA5576A1/uk unknown
- 1980-06-02 SU SU802932704A patent/SU1055331A3/ru active
-
1981
- 1981-10-05 US US06/308,805 patent/US4486354A/en not_active Expired - Lifetime
-
1983
- 1983-04-28 AU AU14051/83A patent/AU566870B2/en not_active Expired
-
1984
- 1984-02-27 US US06/583,286 patent/US4602017A/en not_active Expired - Lifetime
-
1985
- 1985-06-04 JP JP12137085A patent/JPS6133163A/ja active Granted
- 1985-12-30 MY MY62/85A patent/MY8500062A/xx unknown
-
1991
- 1991-12-17 CZ CS913848A patent/CZ384891A3/cs unknown
-
1992
- 1992-06-17 MX MX9202962A patent/MX9202962A/es unknown
-
1993
- 1993-07-29 BG BG097992A patent/BG60427B2/bg unknown
-
1994
- 1994-05-16 GE GEAP19941909A patent/GEP19960470B/en unknown
-
1995
- 1995-04-28 NL NL950007C patent/NL950007I2/nl unknown
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