DE69500660T2 - Ophthalmische Zusammensetzung enthaltend ein 1,5-Benzoxathiepin-Derivat zur Behandlung von Glaukoma - Google Patents
Ophthalmische Zusammensetzung enthaltend ein 1,5-Benzoxathiepin-Derivat zur Behandlung von GlaukomaInfo
- Publication number
- DE69500660T2 DE69500660T2 DE69500660T DE69500660T DE69500660T2 DE 69500660 T2 DE69500660 T2 DE 69500660T2 DE 69500660 T DE69500660 T DE 69500660T DE 69500660 T DE69500660 T DE 69500660T DE 69500660 T2 DE69500660 T2 DE 69500660T2
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- hydrogen
- radical
- lower alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 208000010412 Glaucoma Diseases 0.000 title description 11
- JJBXPFRTXHADRQ-UHFFFAOYSA-N 2h-1,5-benzoxathiepine Chemical class S1C=CCOC2=CC=CC=C21 JJBXPFRTXHADRQ-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 125000002252 acyl group Chemical group 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 10
- 208000030533 eye disease Diseases 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 28
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 230000004410 intraocular pressure Effects 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 208000001953 Hypotension Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 208000021822 hypotensive Diseases 0.000 claims description 15
- 230000001077 hypotensive effect Effects 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical class O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- -1 alkoxy radical Chemical class 0.000 description 86
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 235000002639 sodium chloride Nutrition 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000000921 elemental analysis Methods 0.000 description 31
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 20
- 239000013078 crystal Substances 0.000 description 20
- 239000003889 eye drop Substances 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 229940012356 eye drops Drugs 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 229940126062 Compound A Drugs 0.000 description 14
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000003732 agents acting on the eye Substances 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 229940125702 ophthalmic agent Drugs 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000283973 Oryctolagus cuniculus Species 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 229960005150 glycerol Drugs 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- AZLPEJUVWWGLHA-UHFFFAOYSA-N ethyl acetate;hexane;methanol Chemical compound OC.CCCCCC.CCOC(C)=O AZLPEJUVWWGLHA-UHFFFAOYSA-N 0.000 description 5
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- AQLHJNRNLYDLDP-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperazine Chemical compound C1CN(CCCCl)CCN1C1=CC=CC=C1 AQLHJNRNLYDLDP-UHFFFAOYSA-N 0.000 description 4
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- 229930195725 Mannitol Natural products 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
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- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 239000003885 eye ointment Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
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- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 4
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 3
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP747094 | 1994-01-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69500660D1 DE69500660D1 (de) | 1997-10-16 |
| DE69500660T2 true DE69500660T2 (de) | 1998-02-26 |
Family
ID=11666688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69500660T Expired - Fee Related DE69500660T2 (de) | 1994-01-27 | 1995-01-25 | Ophthalmische Zusammensetzung enthaltend ein 1,5-Benzoxathiepin-Derivat zur Behandlung von Glaukoma |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5538974A (https=) |
| EP (1) | EP0667156B1 (https=) |
| KR (1) | KR950032169A (https=) |
| CN (1) | CN1116928A (https=) |
| AT (1) | ATE157870T1 (https=) |
| CA (1) | CA2141176A1 (https=) |
| DE (1) | DE69500660T2 (https=) |
| ES (1) | ES2106573T3 (https=) |
| TW (1) | TW316235B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| CN1269484C (zh) | 1998-09-18 | 2006-08-16 | 艾尔科实验室公司 | 用于治疗青光眼的5－羟色胺激活性激动剂 |
| US6903081B2 (en) * | 2000-03-31 | 2005-06-07 | Purdue Research Foundation | Phosphoramidates and methods therefor |
| FR2822467B1 (fr) * | 2001-03-22 | 2003-12-12 | Pf Medicament | Derives benzoxathiepines et leur utilisation comme medicaments |
| WO2003051352A1 (en) * | 2001-12-14 | 2003-06-26 | Alcon, Inc. | Aminoalkyl-benzofuran-5-ol compounds for the treatment of glaucoma |
| TW593302B (en) * | 2001-12-20 | 2004-06-21 | Alcon Inc | Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma |
| PT1534391E (pt) * | 2002-07-19 | 2007-05-31 | Biovitrum Ab | Novos derivados e piperazinilo-pirazinona para o tratamento de desordens relacionadas com o receptor 5-ht |
| JP2006501245A (ja) * | 2002-08-30 | 2006-01-12 | アルコン，インコーポレイテッド | 置換された５−クロマン−５−イル−エチルアミン化合物および緑内障の治療のためのその使用 |
| BR0316775A (pt) * | 2002-12-13 | 2005-11-01 | Alcon Inc | Novos análogos de benzopirano e seu uso para o tratamento de glaucoma |
| CA2536185C (en) * | 2003-08-20 | 2012-06-26 | Santen Pharmaceutical Co., Ltd. | Drug delivery system by administrating fine particles to sub-tenon |
| US7476687B2 (en) * | 2003-11-26 | 2009-01-13 | Alcon, Inc. | Substituted furo[2,3-g]indazoles for the treatment of glaucoma |
| TW200520760A (en) * | 2003-12-15 | 2005-07-01 | Alcon Inc | Substituted [1,4] oxazino [2,3-g] indazoles for the treatment of glaucoma |
| US7338972B1 (en) | 2003-12-15 | 2008-03-04 | Alcon, Inc. | Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma |
| US7129257B1 (en) * | 2003-12-15 | 2006-10-31 | Alcon, Inc. | Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma |
| US20050276867A1 (en) | 2004-06-09 | 2005-12-15 | Allergan, Inc. | Stabilized compositions comprising a therapeutically active agent and an oxidizing preservative |
| US7425572B2 (en) * | 2004-12-08 | 2008-09-16 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| TW200744567A (en) * | 2005-09-23 | 2007-12-16 | Alcon Inc | Phenylethylamine analogs and their use for treating glaucoma |
| US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| EP2119436A4 (en) | 2006-10-20 | 2010-03-03 | Ltd Liability Company Mitotech | PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF EYE DISEASES |
| WO2008048135A1 (fr) * | 2006-10-20 | 2008-04-24 | Limited Liability Company 'mitotechnology' | Composition destinée à la régénération, la stimulation de la croissance et l'adaptation de plantes à tous types de facteurs de stress |
| US8349902B2 (en) | 2007-01-29 | 2013-01-08 | Mitotech Sa | Pharmaceutical compositions useful for preventing and treating oncological diseases |
| EP2145623A4 (en) * | 2007-01-29 | 2010-10-27 | Ltd Liability Company Mitotech | PHARMACEUTICAL AND COSMETIC COMPOSITIONS FOR ACCELERATING THE PROCESS OF WOUND HEALING AND OTHER SURFACE INJURIES |
| US8679557B2 (en) * | 2007-02-27 | 2014-03-25 | Sentiss Pharma Private Limited | Synergistic herbal ophthalmic formulation for lowering the intra ocular pressure in case of glaucoma |
| US9439916B2 (en) * | 2007-04-11 | 2016-09-13 | Mitotech Sa | Composition for decelerating the aging in the organism and for extending the life time thereof and the use of said composition |
| US8518915B2 (en) | 2007-06-29 | 2013-08-27 | Mitotech Sa | Use of mitochondrially-addressed compounds for preventing and treating cardiovascular diseases |
| WO2010056145A1 (ru) | 2008-11-12 | 2010-05-20 | Общество С Ограниченной Ответственностью "Митотехнология" | Способ умеренного повышения протонной проводимости биологических мембран при помощи митохондриально- адресованных делокализованных катионов |
| CN102548548B (zh) * | 2009-06-10 | 2017-09-01 | 米拓科技有限公司（卢森堡） | 用于医学和兽医学的眼科药物组合物 |
| MX2012005356A (es) | 2009-11-13 | 2013-01-29 | Obschestvo S Ogranichennoi Otvetstvennostyu Mitotekh | Substancias farmaceuticas basadas en antioxidantes dirigidos a mitocondria. |
| US9320690B2 (en) | 2010-12-20 | 2016-04-26 | Colgate-Palmolive Company | Gelatin encapsulated oral care composition containing hydrophilic active, hydrophobic structuring agent and oil carrier |
| WO2012167236A1 (en) | 2011-06-03 | 2012-12-06 | Mitotech Sa | Oral formulations of mitochondrially-targeted antioxidants and their preparation and use |
| CN112439071B (zh) * | 2019-09-04 | 2022-05-20 | 武汉科福新药有限责任公司 | 透皮促渗组合物及其在噻吗洛尔制剂中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK166779B1 (da) * | 1983-12-14 | 1993-07-12 | Takeda Chemical Industries Ltd | 1,5-benzoxatiepinderivater eller farmaceutisk acceptable salte deraf, samt farmaceutisk praeparat indeholdende en saadan forbindelse |
| EP0229467A1 (en) * | 1985-12-10 | 1987-07-22 | Takeda Chemical Industries, Ltd. | 1,5-Benzoxathiepin derivatives, their production and use |
-
1995
- 1995-01-24 US US08/378,244 patent/US5538974A/en not_active Expired - Fee Related
- 1995-01-25 ES ES95100934T patent/ES2106573T3/es not_active Expired - Lifetime
- 1995-01-25 DE DE69500660T patent/DE69500660T2/de not_active Expired - Fee Related
- 1995-01-25 AT AT95100934T patent/ATE157870T1/de not_active IP Right Cessation
- 1995-01-25 TW TW084100643A patent/TW316235B/zh active
- 1995-01-25 EP EP95100934A patent/EP0667156B1/en not_active Expired - Lifetime
- 1995-01-26 CA CA002141176A patent/CA2141176A1/en not_active Abandoned
- 1995-01-27 KR KR1019950001542A patent/KR950032169A/ko not_active Withdrawn
- 1995-01-27 CN CN95100372A patent/CN1116928A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0667156B1 (en) | 1997-09-10 |
| US5538974A (en) | 1996-07-23 |
| EP0667156A1 (en) | 1995-08-16 |
| ATE157870T1 (de) | 1997-09-15 |
| CA2141176A1 (en) | 1995-07-28 |
| KR950032169A (ko) | 1995-12-20 |
| TW316235B (https=) | 1997-09-21 |
| DE69500660D1 (de) | 1997-10-16 |
| CN1116928A (zh) | 1996-02-21 |
| ES2106573T3 (es) | 1997-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |