JPS6127951A - β−〔２−（ハロゲノベンジル）−フェノキシ〕−エチルアミン誘導体及びこれを含む抗菌性薬剤組成物ならびにこの誘導体の製造法 - Google Patents
β−〔２−（ハロゲノベンジル）−フェノキシ〕−エチルアミン誘導体及びこれを含む抗菌性薬剤組成物ならびにこの誘導体の製造法Info
- Publication number
- JPS6127951A JPS6127951A JP25389784A JP25389784A JPS6127951A JP S6127951 A JPS6127951 A JP S6127951A JP 25389784 A JP25389784 A JP 25389784A JP 25389784 A JP25389784 A JP 25389784A JP S6127951 A JPS6127951 A JP S6127951A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phenoxy
- ethylamine
- carbon atoms
- alkyl group
- 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
- 239000000203 mixture Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 230000001225 therapeutic effect Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000003863 ammonium salts Chemical class 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- -1 1,1,3,3-tetramethyl-butyl Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- LDWOXWYJBHBUMK-UHFFFAOYSA-M benzyl-[2-[2-[(2,4-dichlorophenyl)methyl]-4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethyl]-diethylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C[N+](CC)(CC)CCOC1=CC=C(C(C)(C)CC(C)(C)C)C=C1CC1=CC=C(Cl)C=C1Cl LDWOXWYJBHBUMK-UHFFFAOYSA-M 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 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
- 239000003814 drug Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 229960005475 antiinfective agent Drugs 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- IBACTYXHZRUVJZ-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)methyl]phenoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=CC=CC=C1CC1=CC=C(Cl)C=C1 IBACTYXHZRUVJZ-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical class CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HJYKSBLJFCJWPG-UHFFFAOYSA-N 4-tert-butyl-2-[(2,4-dichlorophenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC=C(O)C(CC=2C(=CC(Cl)=CC=2)Cl)=C1 HJYKSBLJFCJWPG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000008967 Enuresis Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960003769 clofoctol Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8319056A FR2555573A1 (fr) | 1983-11-29 | 1983-11-29 | Derives de b-(2-(halogenobenzyl)-phenoxy)-ethylamine, procede de preparation et utilisation en therapeutique |
| FR8319056 | 1983-11-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6127951A true JPS6127951A (ja) | 1986-02-07 |
| JPS6323185B2 JPS6323185B2 (enExample) | 1988-05-16 |
Family
ID=9294655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25389784A Granted JPS6127951A (ja) | 1983-11-29 | 1984-11-29 | β−〔２−（ハロゲノベンジル）−フェノキシ〕−エチルアミン誘導体及びこれを含む抗菌性薬剤組成物ならびにこの誘導体の製造法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4659741A (enExample) |
| EP (1) | EP0146450B1 (enExample) |
| JP (1) | JPS6127951A (enExample) |
| AT (1) | ATE24891T1 (enExample) |
| AU (1) | AU569927B2 (enExample) |
| CA (1) | CA1222777A (enExample) |
| DE (1) | DE3462030D1 (enExample) |
| DK (1) | DK564384A (enExample) |
| ES (1) | ES8601096A1 (enExample) |
| FR (1) | FR2555573A1 (enExample) |
| GR (1) | GR81064B (enExample) |
| NZ (1) | NZ210371A (enExample) |
| PT (1) | PT79561B (enExample) |
| ZA (1) | ZA849160B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK368687A (da) * | 1986-11-21 | 1988-05-22 | Cheminova As | Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider |
| CN115925585B (zh) * | 2022-04-22 | 2023-11-03 | 广州医科大学 | 氯福克酚衍生物、抗菌药物及制备方法与应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE504409A (enExample) * | ||||
| US2673879A (en) * | 1949-07-30 | 1954-03-30 | Lilly Co Eli | Substituted haloalkylamines |
| US2681933A (en) * | 1949-11-25 | 1954-06-22 | Bristol Lab Inc | Beta-chloroethylamines |
| CH434288A (de) * | 1962-01-18 | 1967-04-30 | Ciba Geigy | Verfahren zur Herstellung neuer Diphenylalkanverbindungen |
| US3488357A (en) * | 1967-04-07 | 1970-01-06 | Ciba Geigy Corp | 2-halophenyl-2-aminoalkoxy-phenylpropanes |
| US3984482A (en) * | 1967-08-31 | 1976-10-05 | Institut De Recherches Chimiques Et Biologiques Appliquees I.R.C.E.B.A. | 2-(Dihalobenzyl)-6-nitro-4-t-butylphenol and preparation thereof |
| US3855317A (en) * | 1967-08-31 | 1974-12-17 | Inst Rech Chim Biolog | 2-4-halobenzyl phenols and preparation thereof |
| US4024282A (en) * | 1975-11-25 | 1977-05-17 | Mitsubishi Chemical Industries Ltd. | Pharmaceutically active 2-(3-alkylaminopropoxy)diphenylmethanes |
| CA1086733A (en) * | 1976-12-06 | 1980-09-30 | Ryoji Kikumoto | Pharmaceutically active 2-substituted-1-(omega- aminoalkoxy) benzenes |
-
1983
- 1983-11-29 FR FR8319056A patent/FR2555573A1/fr not_active Withdrawn
-
1984
- 1984-11-23 EP EP84402387A patent/EP0146450B1/fr not_active Expired
- 1984-11-23 AT AT84402387T patent/ATE24891T1/de not_active IP Right Cessation
- 1984-11-23 ZA ZA849160A patent/ZA849160B/xx unknown
- 1984-11-23 DE DE8484402387T patent/DE3462030D1/de not_active Expired
- 1984-11-26 CA CA000468623A patent/CA1222777A/fr not_active Expired
- 1984-11-27 US US06/675,297 patent/US4659741A/en not_active Expired - Fee Related
- 1984-11-27 AU AU35905/84A patent/AU569927B2/en not_active Ceased
- 1984-11-27 PT PT79561A patent/PT79561B/pt not_active IP Right Cessation
- 1984-11-27 GR GR81064A patent/GR81064B/el unknown
- 1984-11-28 DK DK564384A patent/DK564384A/da not_active Application Discontinuation
- 1984-11-28 NZ NZ210371A patent/NZ210371A/en unknown
- 1984-11-29 ES ES538548A patent/ES8601096A1/es not_active Expired
- 1984-11-29 JP JP25389784A patent/JPS6127951A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2555573A1 (fr) | 1985-05-31 |
| ES538548A0 (es) | 1985-11-01 |
| PT79561A (fr) | 1984-12-01 |
| AU3590584A (en) | 1985-06-06 |
| GR81064B (en) | 1985-03-27 |
| JPS6323185B2 (enExample) | 1988-05-16 |
| ATE24891T1 (de) | 1987-01-15 |
| ZA849160B (en) | 1985-07-31 |
| DK564384D0 (da) | 1984-11-28 |
| DE3462030D1 (en) | 1987-02-19 |
| EP0146450A3 (en) | 1985-07-24 |
| ES8601096A1 (es) | 1985-11-01 |
| NZ210371A (en) | 1988-05-30 |
| AU569927B2 (en) | 1988-02-25 |
| DK564384A (da) | 1985-05-30 |
| PT79561B (fr) | 1986-09-15 |
| EP0146450B1 (fr) | 1987-01-14 |
| CA1222777A (fr) | 1987-06-09 |
| EP0146450A2 (fr) | 1985-06-26 |
| US4659741A (en) | 1987-04-21 |
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