BG62519B1 - 2,3,4,5-тетрахидро-1,4-бензотиазепини, методи за тяхнотополучаване и използването им като терапевтични средства - Google Patents
2,3,4,5-тетрахидро-1,4-бензотиазепини, методи за тяхнотополучаване и използването им като терапевтични средства Download PDFInfo
- Publication number
- BG62519B1 BG62519B1 BG99679A BG9967995A BG62519B1 BG 62519 B1 BG62519 B1 BG 62519B1 BG 99679 A BG99679 A BG 99679A BG 9967995 A BG9967995 A BG 9967995A BG 62519 B1 BG62519 B1 BG 62519B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- benzothiazepine
- tetrahydro
- formula
- chloro
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 title abstract description 50
- 238000009472 formulation Methods 0.000 title abstract description 3
- 230000001225 therapeutic effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- -1 imino, methylimino, phenylimino Chemical group 0.000 claims abstract description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 11
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 10
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 10
- 206010015037 epilepsy Diseases 0.000 claims abstract description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 7
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 3
- 230000000324 neuroprotective effect Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 206010010904 Convulsion Diseases 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- KYVHGCKMVJDCNV-UHFFFAOYSA-N 1,4-benzothiazepine Chemical compound S1C=CN=CC2=CC=CC=C12 KYVHGCKMVJDCNV-UHFFFAOYSA-N 0.000 claims description 11
- SGHFCTZTSKLZLQ-UHFFFAOYSA-N 6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine Chemical compound S1CCNCC2=C1C=CC=C2Cl SGHFCTZTSKLZLQ-UHFFFAOYSA-N 0.000 claims description 11
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- 239000004090 neuroprotective agent Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- NABPZJKIWLALLY-UHFFFAOYSA-N n-(6-chloro-2,5-dihydro-1,4-benzothiazepin-3-yl)hydroxylamine Chemical compound C1NC(=NO)CSC2=CC=CC(Cl)=C21 NABPZJKIWLALLY-UHFFFAOYSA-N 0.000 claims description 6
- PBUVSAUCKUNQRD-UHFFFAOYSA-N 1-(6-chloro-1-oxo-3,5-dihydro-2h-1$l^{4},4-benzothiazepin-4-yl)ethanone Chemical compound C1N(C(=O)C)CCS(=O)C2=CC=CC(Cl)=C21 PBUVSAUCKUNQRD-UHFFFAOYSA-N 0.000 claims description 5
- IYNOWXHALNJVTD-UHFFFAOYSA-N 6-chloro-2,3,4,5-tetrahydro-1$l^{4},4-benzothiazepine 1-oxide Chemical compound C1NCCS(=O)C2=C1C(Cl)=CC=C2 IYNOWXHALNJVTD-UHFFFAOYSA-N 0.000 claims description 5
- YAZUSGHZMAPMQE-UHFFFAOYSA-N 6-fluoro-2,3,4,5-tetrahydro-1,4-benzothiazepine Chemical compound S1CCNCC2=C1C=CC=C2F YAZUSGHZMAPMQE-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
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- UREQFTSPNGUYSJ-UHFFFAOYSA-N 1-(3,5-dihydro-2h-1,4-benzothiazepin-4-yl)ethanone Chemical compound C1N(C(=O)C)CCSC2=CC=CC=C21 UREQFTSPNGUYSJ-UHFFFAOYSA-N 0.000 claims description 4
- ISNYZTVJXZYPCX-UHFFFAOYSA-N 3,5-dihydro-2h-1,4-benzothiazepine-4-carbaldehyde Chemical compound C1N(C=O)CCSC2=CC=CC=C21 ISNYZTVJXZYPCX-UHFFFAOYSA-N 0.000 claims description 4
- DPMRVEKZRBXCIW-UHFFFAOYSA-N 6-chloro-4-methylsulfinyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound C1N(S(=O)C)CCSC2=CC=CC(Cl)=C21 DPMRVEKZRBXCIW-UHFFFAOYSA-N 0.000 claims description 4
- NTHZSPUSDHLYTG-UHFFFAOYSA-N 6-chloro-4-methylsulfonyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound C1N(S(=O)(=O)C)CCSC2=CC=CC(Cl)=C21 NTHZSPUSDHLYTG-UHFFFAOYSA-N 0.000 claims description 4
- GAQRNLNAUIIXEZ-UHFFFAOYSA-N 6-chloro-n-phenyl-2,5-dihydro-1,4-benzothiazepin-3-amine Chemical compound N1CC=2C(Cl)=CC=CC=2SCC1=NC1=CC=CC=C1 GAQRNLNAUIIXEZ-UHFFFAOYSA-N 0.000 claims description 4
- ZSOSRXSUDMSECL-UHFFFAOYSA-N 6-methyl-2,3,4,5-tetrahydro-1,4-benzothiazepine Chemical compound S1CCNCC2=C1C=CC=C2C ZSOSRXSUDMSECL-UHFFFAOYSA-N 0.000 claims description 4
- RGJIRNUNNWORFL-UHFFFAOYSA-N n-(6-methyl-2,5-dihydro-1,4-benzothiazepin-3-yl)hydroxylamine Chemical compound S1CC(=NO)NCC2=C1C=CC=C2C RGJIRNUNNWORFL-UHFFFAOYSA-N 0.000 claims description 4
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- RCZYGXYJABXFPK-UHFFFAOYSA-N 1-(1-oxo-3,5-dihydro-2h-1$l^{4},4-benzothiazepin-4-yl)ethanone Chemical compound C1N(C(=O)C)CCS(=O)C2=CC=CC=C21 RCZYGXYJABXFPK-UHFFFAOYSA-N 0.000 claims description 3
- ZTNADGMRKJZOJT-UHFFFAOYSA-N 1-(3,5-dihydro-2h-1,4-benzothiazepin-4-yl)propan-1-one Chemical compound C1N(C(=O)CC)CCSC2=CC=CC=C21 ZTNADGMRKJZOJT-UHFFFAOYSA-N 0.000 claims description 3
- HEFUIQDDJAUWNE-UHFFFAOYSA-N 1-(6-chloro-3,5-dihydro-2h-1,4-benzothiazepin-4-yl)propan-1-one Chemical compound C1N(C(=O)CC)CCSC2=CC=CC(Cl)=C21 HEFUIQDDJAUWNE-UHFFFAOYSA-N 0.000 claims description 3
- XRHNTUDLOFKUFB-UHFFFAOYSA-N 4-ethylsulfonyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound C1N(S(=O)(=O)CC)CCSC2=CC=CC=C21 XRHNTUDLOFKUFB-UHFFFAOYSA-N 0.000 claims description 3
- VQGBJTNOBPJBCI-UHFFFAOYSA-N 6-chloro-4-ethylsulfonyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound C1N(S(=O)(=O)CC)CCSC2=CC=CC(Cl)=C21 VQGBJTNOBPJBCI-UHFFFAOYSA-N 0.000 claims description 3
- YNEUTBJJWJUGNL-UHFFFAOYSA-N 6-chloro-4-methylsulfonyl-3,5-dihydro-2h-1$l^{4},4-benzothiazepine 1-oxide Chemical compound C1N(S(=O)(=O)C)CCS(=O)C2=CC=CC(Cl)=C21 YNEUTBJJWJUGNL-UHFFFAOYSA-N 0.000 claims description 3
- QKIVZDWLNQMALJ-UHFFFAOYSA-N 6-fluoro-4-methylsulfonyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound C1N(S(=O)(=O)C)CCSC2=CC=CC(F)=C21 QKIVZDWLNQMALJ-UHFFFAOYSA-N 0.000 claims description 3
- SAWVIKJOESZFIK-UHFFFAOYSA-N 6-methyl-4-methylsulfonyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound S1CCN(S(C)(=O)=O)CC2=C1C=CC=C2C SAWVIKJOESZFIK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
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- XSKMMXNLEXKYOY-UHFFFAOYSA-N n-(2,5-dihydro-1,4-benzothiazepin-3-yl)hydroxylamine Chemical compound C1NC(=NO)CSC2=CC=CC=C21 XSKMMXNLEXKYOY-UHFFFAOYSA-N 0.000 claims description 3
- MRHCFUAGRDCRIP-UHFFFAOYSA-N n-methyl-2,5-dihydro-1,4-benzothiazepin-3-amine Chemical compound C1NC(=NC)CSC2=CC=CC=C21 MRHCFUAGRDCRIP-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
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- UVLUXVGGWULYRA-UHFFFAOYSA-N (6-chloro-3,5-dihydro-2h-1,4-benzothiazepin-4-yl)-phenylmethanone Chemical compound C1C=2C(Cl)=CC=CC=2SCCN1C(=O)C1=CC=CC=C1 UVLUXVGGWULYRA-UHFFFAOYSA-N 0.000 claims description 2
- SKXSNICLTSJDDZ-UHFFFAOYSA-N 1-(6-methyl-3,5-dihydro-2h-1,4-benzothiazepin-4-yl)ethanone Chemical compound C1N(C(=O)C)CCSC2=CC=CC(C)=C21 SKXSNICLTSJDDZ-UHFFFAOYSA-N 0.000 claims description 2
- BJWRKQPKTFGOSR-UHFFFAOYSA-N 6-chloro-n-methoxy-2,5-dihydro-1,4-benzothiazepin-3-amine Chemical compound C1NC(=NOC)CSC2=CC=CC(Cl)=C21 BJWRKQPKTFGOSR-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003085 diluting agent Substances 0.000 claims description 2
- JPGSKUHVFVQTAA-UHFFFAOYSA-N n-methoxy-2,5-dihydro-1,4-benzothiazepin-3-amine Chemical compound C1NC(=NOC)CSC2=CC=CC=C21 JPGSKUHVFVQTAA-UHFFFAOYSA-N 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 8
- GQKWMROFTREIMB-UHFFFAOYSA-N 4-methylsulfonyl-3,5-dihydro-2h-1,4-benzothiazepine Chemical compound C1N(S(=O)(=O)C)CCSC2=CC=CC=C21 GQKWMROFTREIMB-UHFFFAOYSA-N 0.000 claims 3
- AQEDFPDRXSRDPJ-UHFFFAOYSA-N 1-(6-fluoro-3,5-dihydro-2h-1,4-benzothiazepin-4-yl)ethanone Chemical compound C1N(C(=O)C)CCSC2=CC=CC(F)=C21 AQEDFPDRXSRDPJ-UHFFFAOYSA-N 0.000 claims 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- DBUISKTZMAMFFW-UHFFFAOYSA-N thiazepin-3-one Chemical compound O=C1NSC=CC=C1 DBUISKTZMAMFFW-UHFFFAOYSA-N 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929223441A GB9223441D0 (en) | 1992-11-09 | 1992-11-09 | Therapeutic agents |
| GB929223443A GB9223443D0 (en) | 1992-11-09 | 1992-11-09 | Therapeutic agents |
| PCT/EP1993/003123 WO1994011360A1 (en) | 1992-11-09 | 1993-11-06 | 1,4-benzothiazepines useful as neurological agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG99679A BG99679A (bg) | 1996-04-30 |
| BG62519B1 true BG62519B1 (bg) | 2000-01-31 |
Family
ID=26301938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG99679A BG62519B1 (bg) | 1992-11-09 | 1995-05-30 | 2,3,4,5-тетрахидро-1,4-бензотиазепини, методи за тяхнотополучаване и използването им като терапевтични средства |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5580866A (cs) |
| EP (1) | EP0667866B1 (cs) |
| JP (1) | JPH08503202A (cs) |
| KR (1) | KR100313649B1 (cs) |
| AT (1) | ATE163927T1 (cs) |
| BG (1) | BG62519B1 (cs) |
| BR (1) | BR9307387A (cs) |
| CA (1) | CA2148584A1 (cs) |
| CZ (1) | CZ288595B6 (cs) |
| DE (1) | DE69317436T2 (cs) |
| DK (1) | DK0667866T3 (cs) |
| ES (1) | ES2113081T3 (cs) |
| FI (1) | FI952204A7 (cs) |
| GR (1) | GR3026386T3 (cs) |
| HU (1) | HUT71819A (cs) |
| NO (1) | NO304467B1 (cs) |
| NZ (1) | NZ257843A (cs) |
| PL (1) | PL179401B1 (cs) |
| RU (1) | RU2115650C1 (cs) |
| SK (1) | SK280522B6 (cs) |
| UA (1) | UA41342C2 (cs) |
| WO (1) | WO1994011360A1 (cs) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5939412A (en) * | 1992-06-26 | 1999-08-17 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| PT100631B (pt) * | 1991-06-28 | 1999-06-30 | Smithkline Beecham Corp | Antagonistas biciclicos de fibrinogenio, seu uso e composicoes farmaceuticas que os contem |
| MA23420A1 (fr) * | 1994-01-07 | 1995-10-01 | Smithkline Beecham Corp | Antagonistes bicycliques de fibrinogene. |
| US6458784B1 (en) | 1994-06-29 | 2002-10-01 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| GB9506382D0 (en) * | 1995-03-29 | 1995-05-17 | Boots Co Plc | Pharmaceutical compositions |
| US5977101A (en) * | 1995-06-29 | 1999-11-02 | Smithkline Beecham Corporation | Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity |
| ZA9610853B (en) | 1995-12-29 | 1998-04-06 | Smithkline Beecham Corp | Processes and intermediates for preparing pharmaceuticals. |
| GB9616279D0 (en) * | 1996-08-02 | 1996-09-11 | Knoll Ag | Chemical process |
| ATE242258T1 (de) * | 1997-03-14 | 2003-06-15 | Aventis Pharma Gmbh | Hypolipidemische 1,4-benzothiazepin-1,1-dioxide |
| GB9914745D0 (en) * | 1999-06-24 | 1999-08-25 | Knoll Ag | Therapeutic agents |
| GB9922271D0 (en) * | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Formulation |
| US7718644B2 (en) * | 2004-01-22 | 2010-05-18 | The Trustees Of Columbia University In The City Of New York | Anti-arrhythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) and uses thereof |
| US20040229781A1 (en) * | 2000-05-10 | 2004-11-18 | Marks Andrew Robert | Compounds and methods for treating and preventing exercise-induced cardiac arrhythmias |
| US8022058B2 (en) | 2000-05-10 | 2011-09-20 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| US7879840B2 (en) | 2005-08-25 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| US7393652B2 (en) | 2000-05-10 | 2008-07-01 | The Trustees Of Columbia University In The City Of New York | Methods for identifying a chemical compound that directly enhances binding of FKBP12.6 to PKA-phosphorylated type 2 ryanodine receptor (RyR2) |
| US7544678B2 (en) | 2002-11-05 | 2009-06-09 | The Trustees Of Columbia University In The City Of New York | Anti-arrythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) |
| AU2004220548A1 (en) | 2003-03-07 | 2004-09-23 | The Trustees Of Columbia University, In The City Of New York | Type 1 ryanodine receptor-based methods |
| US8710045B2 (en) | 2004-01-22 | 2014-04-29 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the ryanodine receptors |
| US7704990B2 (en) * | 2005-08-25 | 2010-04-27 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| NZ587767A (en) | 2008-03-03 | 2012-05-25 | Servier Lab | Process for preparing benzothiazepines from gamma-aminoalkylbenzenes |
| WO2013064231A1 (en) | 2011-10-31 | 2013-05-10 | Phenex Pharmaceuticals Ag | SEVEN-MEMBERED SULFONAMIDES AS MODULATORS OF RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORγ, NR1F3) |
| EP2708535A1 (en) | 2012-05-11 | 2014-03-19 | Les Laboratoires Servier | Agents for treating disorders involving modulation of ryanodine receptors |
| KR102157141B1 (ko) | 2018-11-27 | 2020-09-17 | 주식회사 파미니티 | 으아리 추출물을 유효 성분으로 포함하는 인지 기능 개선용 조성물 |
| KR102172916B1 (ko) | 2018-12-07 | 2020-11-02 | 주식회사 파미니티 | 실크 펩타이드 및 천연 추출물을 포함하는 인지 기능 개선용 조성물 |
| JP2023549583A (ja) * | 2020-11-17 | 2023-11-27 | アームゴ・ファーマ・インコーポレーテッド | リアノジン受容体関連障害治療用薬剤 |
| CN116887839A (zh) | 2021-01-08 | 2023-10-13 | 阿姆果制药有限公司 | 兰诺定受体调节剂的结晶形式及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362962A (en) * | 1964-01-24 | 1968-01-09 | Hoffmann La Roche | Certain benzothiazepine derivatives |
| US3682962A (en) * | 1970-03-17 | 1972-08-08 | Sterling Drug Inc | 1-substituted-1,2,3,5-tetrahydro-4,1-benzothiozepines |
| EP0368063B1 (de) * | 1988-11-05 | 1992-06-10 | Bayer Ag | Verfahren zur Kernchlorierung von aromatischen Kohlenwasserstoffen |
| JP2703408B2 (ja) * | 1990-12-28 | 1998-01-26 | 麒麟麦酒株式会社 | １，４‐ベンゾチアゼピン誘導体 |
| GB9111376D0 (en) * | 1991-05-25 | 1991-07-17 | Boots Co Plc | Therapeutic agents |
| GB9203347D0 (en) * | 1992-02-17 | 1992-04-01 | Wellcome Found | Hypolipidaemic compounds |
-
1993
- 1993-11-06 UA UA95062705A patent/UA41342C2/uk unknown
- 1993-11-06 BR BR9307387-9A patent/BR9307387A/pt not_active Application Discontinuation
- 1993-11-06 PL PL93308757A patent/PL179401B1/pl unknown
- 1993-11-06 ES ES94900113T patent/ES2113081T3/es not_active Expired - Lifetime
- 1993-11-06 KR KR1019950701831A patent/KR100313649B1/ko not_active Expired - Fee Related
- 1993-11-06 NZ NZ257843A patent/NZ257843A/en unknown
- 1993-11-06 AT AT94900113T patent/ATE163927T1/de not_active IP Right Cessation
- 1993-11-06 CZ CZ19951176A patent/CZ288595B6/cs not_active IP Right Cessation
- 1993-11-06 CA CA002148584A patent/CA2148584A1/en not_active Abandoned
- 1993-11-06 RU RU95112484/04A patent/RU2115650C1/ru not_active IP Right Cessation
- 1993-11-06 WO PCT/EP1993/003123 patent/WO1994011360A1/en active IP Right Grant
- 1993-11-06 HU HU9501352A patent/HUT71819A/hu unknown
- 1993-11-06 DE DE69317436T patent/DE69317436T2/de not_active Expired - Fee Related
- 1993-11-06 EP EP94900113A patent/EP0667866B1/en not_active Expired - Lifetime
- 1993-11-06 US US08/424,464 patent/US5580866A/en not_active Expired - Fee Related
- 1993-11-06 DK DK94900113.5T patent/DK0667866T3/da active
- 1993-11-06 SK SK588-95A patent/SK280522B6/sk unknown
- 1993-11-06 JP JP6511695A patent/JPH08503202A/ja not_active Withdrawn
-
1995
- 1995-05-08 NO NO951797A patent/NO304467B1/no not_active IP Right Cessation
- 1995-05-08 FI FI952204A patent/FI952204A7/fi unknown
- 1995-05-30 BG BG99679A patent/BG62519B1/bg unknown
-
1998
- 1998-03-17 GR GR980400582T patent/GR3026386T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69317436T2 (de) | 1998-07-02 |
| KR950704283A (ko) | 1995-11-17 |
| PL179401B1 (pl) | 2000-08-31 |
| EP0667866A1 (en) | 1995-08-23 |
| NZ257843A (en) | 1996-10-28 |
| BG99679A (bg) | 1996-04-30 |
| CA2148584A1 (en) | 1994-05-26 |
| US5580866A (en) | 1996-12-03 |
| KR100313649B1 (ko) | 2002-02-28 |
| FI952204A0 (fi) | 1995-05-08 |
| NO951797D0 (no) | 1995-05-08 |
| JPH08503202A (ja) | 1996-04-09 |
| NO951797L (no) | 1995-05-24 |
| NO304467B1 (no) | 1998-12-21 |
| RU95112484A (ru) | 1997-04-20 |
| UA41342C2 (uk) | 2001-09-17 |
| ATE163927T1 (de) | 1998-03-15 |
| FI952204A7 (fi) | 1995-05-08 |
| RU2115650C1 (ru) | 1998-07-20 |
| CZ288595B6 (cs) | 2001-07-11 |
| GR3026386T3 (en) | 1998-06-30 |
| PL308757A1 (en) | 1995-08-21 |
| BR9307387A (pt) | 1999-08-31 |
| DK0667866T3 (da) | 1998-05-25 |
| AU680639B2 (en) | 1997-08-07 |
| HU9501352D0 (en) | 1995-06-28 |
| HUT71819A (en) | 1996-02-28 |
| SK58895A3 (en) | 1995-09-13 |
| DE69317436D1 (de) | 1998-04-16 |
| EP0667866B1 (en) | 1998-03-11 |
| WO1994011360A1 (en) | 1994-05-26 |
| CZ117695A3 (en) | 1996-06-12 |
| AU5464494A (en) | 1994-06-08 |
| ES2113081T3 (es) | 1998-04-16 |
| SK280522B6 (sk) | 2000-03-13 |
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