JPS58154538A - アルキルアミノアルコ−ル誘導体、その製造法、並びに該誘導体を有効成分とする新規薬剤 - Google Patents
アルキルアミノアルコ−ル誘導体、その製造法、並びに該誘導体を有効成分とする新規薬剤Info
- Publication number
- JPS58154538A JPS58154538A JP58026112A JP2611283A JPS58154538A JP S58154538 A JPS58154538 A JP S58154538A JP 58026112 A JP58026112 A JP 58026112A JP 2611283 A JP2611283 A JP 2611283A JP S58154538 A JPS58154538 A JP S58154538A
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- butylamino
- propan
- compound
- oximino
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 8
- 229940079593 drug Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- -1 alkylamine alcohol derivative Chemical class 0.000 claims description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 239000001530 fumaric acid Substances 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000007951 isotonicity adjuster Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000003889 eye drop Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 229940012356 eye drops Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000002923 oximes Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000004410 intraocular pressure Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 241000238557 Decapoda Species 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000001089 Multiple system atrophy Diseases 0.000 description 2
- 206010031127 Orthostatic hypotension Diseases 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000001384 anti-glaucoma Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 208000030533 eye disease Diseases 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical class O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000065675 Cyclops Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 108010027597 alpha-chymotrypsin Proteins 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000000030 antiglaucoma agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000004493 normal intraocular pressure Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 102200155797 rs28933378 Human genes 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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
- A61K31/13—Amines
- A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
-
- 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
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8202740 | 1982-02-19 | ||
| FR8202740A FR2521856A1 (fr) | 1982-02-19 | 1982-02-19 | Medicament ophtalmique pour le traitement des glaucomes, a base d'ethers-oxydes ou d'ether-oximes de derives alcoylamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58154538A true JPS58154538A (ja) | 1983-09-14 |
| JPH0427976B2 JPH0427976B2 (cg-RX-API-DMAC10.html) | 1992-05-13 |
Family
ID=9271145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58026112A Granted JPS58154538A (ja) | 1982-02-19 | 1983-02-18 | アルキルアミノアルコ−ル誘導体、その製造法、並びに該誘導体を有効成分とする新規薬剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4766151A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0087378B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS58154538A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE38150T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU571434B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1242458A (cg-RX-API-DMAC10.html) |
| DE (1) | DE3378300D1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2521856A1 (cg-RX-API-DMAC10.html) |
| IE (1) | IE55328B1 (cg-RX-API-DMAC10.html) |
| IN (1) | IN159333B (cg-RX-API-DMAC10.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6468348A (en) * | 1987-08-19 | 1989-03-14 | Merck & Co Inc | Amino-2-hydroxypropyloxyiminoheterocycle beta insulator |
| US5347624A (en) * | 1987-03-05 | 1994-09-13 | Hitachi, Ltd. | Method and apparatus for display control |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3704604A1 (de) * | 1987-02-13 | 1988-08-25 | Mack Chem Pharm | Oximether von 2,6-dioxabicyclo(3.3.0)octanonen, herstellungsverfahren und anwendung als arzneimittel |
| US5234934A (en) * | 1989-08-25 | 1993-08-10 | Egis Gyogyszergyar | Aminopropanol derivatives, process for their preparation and pharmaceutical compositions comprising the same |
| HU212415B (en) * | 1989-08-25 | 1996-06-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new cyclic oxym derivatives and pharmaceutical compositions containing them as active components |
| IL97759A0 (en) * | 1990-04-11 | 1992-06-21 | Ciba Geigy Ag | Hydroxylamine compounds |
| US5629345A (en) * | 1993-07-23 | 1997-05-13 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| US5965620A (en) * | 1993-07-23 | 1999-10-12 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| CA2272308C (en) * | 1996-12-13 | 2007-01-16 | Alcon Laboratories, Inc. | Use of low molecular weight amino alcohols in ophthalmic compositions |
| US6491039B1 (en) | 1998-01-23 | 2002-12-10 | Innercool Therapies, Inc. | Medical procedure |
| US8377459B2 (en) * | 2003-07-09 | 2013-02-19 | The Procter & Gamble Company | Composition for wet wipes that enhances the efficacy of cleansing while being gentle to the skin |
| JP5108234B2 (ja) * | 2005-02-07 | 2012-12-26 | 日本特殊陶業株式会社 | マイクロヒータ及びセンサ |
| US7313928B2 (en) * | 2005-07-15 | 2008-01-01 | Lucien Girard | Insert for cooler |
| CN114394913B (zh) * | 2021-12-30 | 2023-02-03 | 山东农业大学 | 一种肟醚衍生物的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2558285A1 (de) * | 1975-12-23 | 1977-07-07 | Dso Pharmachim | Aetherderivate des 3-amino-1,2- propandiols |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1531420A (en) * | 1975-12-29 | 1978-11-08 | Dso Pharmachim | Ether derivatives of 3-amino-1,2-propandiol and salts thereof having beta-adrenergic blocking activity |
| FR2479812A1 (fr) * | 1980-04-04 | 1981-10-09 | Fabre Sa Pierre | Cycloalcoyl propanol amines utiles comme medicaments et procede pour leur preparation |
| FR2479813A1 (fr) * | 1980-04-04 | 1981-10-09 | Fabre Sa Pierre | Alcoxy propanolamines utiles comme medicaments et procede pour leur preparation |
-
1982
- 1982-02-19 FR FR8202740A patent/FR2521856A1/fr active Granted
-
1983
- 1983-02-11 EP EP83440013A patent/EP0087378B1/fr not_active Expired
- 1983-02-11 DE DE8383440013T patent/DE3378300D1/de not_active Expired
- 1983-02-11 AT AT83440013T patent/ATE38150T1/de not_active IP Right Cessation
- 1983-02-17 IN IN104/DEL/83A patent/IN159333B/en unknown
- 1983-02-18 CA CA000421917A patent/CA1242458A/fr not_active Expired
- 1983-02-18 JP JP58026112A patent/JPS58154538A/ja active Granted
- 1983-02-18 AU AU11672/83A patent/AU571434B2/en not_active Ceased
- 1983-02-21 IE IE356/83A patent/IE55328B1/en not_active IP Right Cessation
-
1985
- 1985-10-21 US US06/788,694 patent/US4766151A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2558285A1 (de) * | 1975-12-23 | 1977-07-07 | Dso Pharmachim | Aetherderivate des 3-amino-1,2- propandiols |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5347624A (en) * | 1987-03-05 | 1994-09-13 | Hitachi, Ltd. | Method and apparatus for display control |
| JPS6468348A (en) * | 1987-08-19 | 1989-03-14 | Merck & Co Inc | Amino-2-hydroxypropyloxyiminoheterocycle beta insulator |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2521856A1 (fr) | 1983-08-26 |
| CA1242458A (fr) | 1988-09-27 |
| IE830356L (en) | 1983-08-19 |
| AU1167283A (en) | 1983-08-25 |
| AU571434B2 (en) | 1988-04-21 |
| EP0087378A3 (en) | 1984-07-04 |
| FR2521856B1 (cg-RX-API-DMAC10.html) | 1984-09-07 |
| IN159333B (cg-RX-API-DMAC10.html) | 1987-05-02 |
| JPH0427976B2 (cg-RX-API-DMAC10.html) | 1992-05-13 |
| US4766151A (en) | 1988-08-23 |
| DE3378300D1 (en) | 1988-12-01 |
| EP0087378B1 (fr) | 1988-10-26 |
| ATE38150T1 (de) | 1988-11-15 |
| EP0087378A2 (fr) | 1983-08-31 |
| IE55328B1 (en) | 1990-08-15 |
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