IE54987B1 - Benzhydrylsulfinylethylamine derivatives - Google Patents
Benzhydrylsulfinylethylamine derivativesInfo
- Publication number
- IE54987B1 IE54987B1 IE1249/83A IE124983A IE54987B1 IE 54987 B1 IE54987 B1 IE 54987B1 IE 1249/83 A IE1249/83 A IE 1249/83A IE 124983 A IE124983 A IE 124983A IE 54987 B1 IE54987 B1 IE 54987B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- amine derivative
- acid addition
- addition salt
- given
- Prior art date
Links
- SHMYXVVITSBKCM-UHFFFAOYSA-N 2-benzhydrylsulfinylethanamine Chemical class C=1C=CC=CC=1C([S+]([O-])CCN)C1=CC=CC=C1 SHMYXVVITSBKCM-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- BIPNUYXEYOEPHN-UHFFFAOYSA-N 2-benzhydrylsulfanylethanamine Chemical compound C=1C=CC=CC=1C(SCCN)C1=CC=CC=C1 BIPNUYXEYOEPHN-UHFFFAOYSA-N 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- ORKZATPRQQSLDT-UHFFFAOYSA-N diphenylmethanethiol Chemical compound C=1C=CC=CC=1C(S)C1=CC=CC=C1 ORKZATPRQQSLDT-UHFFFAOYSA-N 0.000 claims description 3
- YGRSUHBDNJJFSD-UHFFFAOYSA-N 2-benzhydrylsulfinyl-n-methylethanamine Chemical compound C=1C=CC=CC=1C(S(=O)CCNC)C1=CC=CC=C1 YGRSUHBDNJJFSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 210000003169 central nervous system Anatomy 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- QFOIDHLIVYBINE-UHFFFAOYSA-N 2-benzhydrylsulfanyl-n-methylethanamine Chemical compound C=1C=CC=CC=1C(SCCNC)C1=CC=CC=C1 QFOIDHLIVYBINE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QGCYWVJSFGJYEX-UHFFFAOYSA-N 1-(2-benzhydrylsulfinylethyl)piperidine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)S(=O)CCN1CCCCC1 QGCYWVJSFGJYEX-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010021113 Hypothermia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007379 Muscle Hypotonia Diseases 0.000 description 1
- 208000027419 Muscular hypotonia Diseases 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010042008 Stereotypy Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000002539 anti-aggressive effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1. Derivatives of N-(benzhydrylsulfinylalkyl)- amine, characterized in that they are selected from among the group constituted by : a) the N-[2-(benzhydrylsulfinyl)ethyl]amines of general formula (I) see diagramm : EP0097546,P4,F2 (wherein R represents a C1 -C4 alkyl group), and b) their acid addition salts.
Description
2 54987 The present invention relates to benzhydrylsulfinylethylamines as industrial products. It also relates to the use of these products in therapeutics and to the method for preparing them. 15 The hydrochloride of N-[2-(benzhydrylsu!finyl)-ethyl]-amine is known to have been described as intermediary of synthesis of disulfide -sulfoxide derivatives by R. G. H1SKEY et al., 3. Org. Chem., 32, pages 3191-319Ψ (1967) without a study of its possible therapeutical properties. It is also known that French Patent No. 76 29137 and corresponding U.S. Patent No. 9 066 686 propose derivatives of the N-(benz-hydrylsulfinylalkyO-amine type, particularly as substances active on the central nervous system (CNS). It has just been unexpectedly found that new derivatives of N-(benzhydryIsulfinylalkyl)-amine present interesting neuropsychopharmacological properties with respect to the products of Examples and 5 of the above-mentioned Patents, namely N-[2-(benzhydryIsulfinyl)-ethyl]-morphoIine and N-[2-(benzhydryl-sulfinyl)-ethyl]-piperidine.
The M-benzhydrylsulfinylalky1-amine derivatives according to the invention are characterized in that they are selected from a) N-[2-(benzhydrylsulfinyi)-ethyl]-amines of the formula CH - SO - ch2 - ch2 - NH - R (I) (wherein R is a Cj-C^-alkyl group), and b) acid addition salts thereof.
Among the R groups included in the definition given hereinabove, particular mention may be made of the CH^, C^Hj, i-C^H^ and t-C^Hg groups.
The most interesting compound from the psychopharmeutical 354987 point of view is the compound R = CHy Among suitable acid addition salts, particular mention may be made of the non-toxic addition salts obtained by reacting the free base of formula I with an inorganic or organic acid. From those acids 5 suitable to this end, particular mention may be made of hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, picric, formic, acetic, propionic, fumaric, maleic, malic, tartaric, citric, oxalic, benzoic, cinnamic ascorbic, methanesulfonic, paratoiuenesulfonic, aspartic and glutamic adds.
The products of formula I are active on the CNS: they act as antidepressants of the CNS and present an interesting anti-aggressive effect.
A therapeutical composition is recommended which is characterized in that it contains, in association with a physiologically acceptable 15 excipient, at least one compound of formula 1 or one of its non-toxic addition salts, as active ingredient! The compounds of formula I may be prepared in accordance with a method known per se by application of conventional reaction mechanisms. The method recommended according to the invention whic h is illustrated by the scheme: (C6H5)2CH - SH + Br-CH2CH2-NHR J (C6H5)2C.H-S-CH2CH2-NHR (11) (III) (IV) (CgH5)2CH-SO-CH2CH2-NHR 25 is characterized in that, successively, (I) a) diphenylmethanethiol (II) is reacted in water, in the presence of a base particularly selected from NaOH and KOH, with a 2-bromo-ethyiamine of formula Br-CH^CH^-NHR (III) - wherein R is defined as indicated hereinabove - under refluxing for at least 1 hour, using 30 from 1 to 1.2 mole of III for 1 mole of II, to obtain a benzhydryithioethyi-amine of formula: 4 54987 (CgH5)2CH - S - CH2CH2 - NHR (IV) then, b) the benzhydrylthioethylamine thus obtained is oxidized in acetic acid with H2C>2 at 110-130 volumes, at a temperature oi 5 W-15°C for J hour.
A certain number of N-[2-(benzhydrylsulfinyi)-ethyl]-amines according to the invention are given in non-limiting manner in Table I hereinbelow: TABLE 1 (CgH5)2CH - SO - CH2CH2 - NHR Product Code No. R Melting point Ex 1 (a) CRL ¢0883 ch3 128-130°C Ex 2 (a) - ch(ch3)2 - Ex 3 (a) Note: (a) : hydrochloride c(ch3)3 Other advantages and features of the invention will be more readily understood on reading the following description of examples of preparation which are in no way limiting.
Preparation I 2o Obtaining of the hydrochloride of N-[2-(benzhydrylsulfinyl)-ethyl]- methylamine (Example I; Code No. : CRL ¢0883). 1) - Hydrochloride of N-[2-(benzhydryIthio)-ethyl]-methylamine. g (0.075 mol) of diphcnylmethanethiol in suspension in 25 75 ml of water are salified with 16 g (0Λ mol) of sodium hydroxide in pellet form in solution in 25 ml of water. The mixture is taken to reflux and a solution of 17.6 g (0.08 mol) of hydrobromide of N-(2-bromoethyO-methylamine in 50 ml of water is poured drop by drop 5 5 54987 into this mixture. Reflux is maintained for 1 hour, the mixture is cooled, extracted with ether, washed in water. The ethereal solution is extracted with 100 ml of 2 N HC1 acid, the base is precipitated with concentrated NaOH. The base is taken up in ether, the ethereal phase is washed in water, dried and the desired hydrochloride is precipitated by the addition of hydrochloric ethanol. The precipitate is drained, washed with ethyl acetate and, by recrystallization from ethanol, the hydrochloride of N-[2-(benzhydrylthio)-ethyl]-methylamine is obtained with a yield of 71%. m.p. 121-122°C. 2) CRL »0883 14 g (0.05 mol) of hydrochloride of N-[2-(benzhydrylthio)-ethyl]-methylamine in solution in 50 ml of acetic acid are oxidized with 5 ml of 2 at volumes for 1 hour at 40°C. The acetic acid is evaporated in vacuo, the residue of evaporation is taken up in acetone and the precipitate formed is drained. By recrystallization from the ethanol-ethyl acetate (1:1) v/v mixture, CRL 40883 is obtained with a yield of 58%. m.p. = 128-I30°C.
The results of the neuropsychopharmacological tests undertaken with CRL 40883 (product of Example I) have been summarized hereinafter. In these tests, CRL 40883 in solution in distilled water at pH 5 was administered by the intraperitoneal route in a volume of 20 ml/kg in the male mouse and in a volume of 5 ml/kg in the male rat.
A - TOXICITY In the male mouse, the LD-30 of CRL 40883 by the IP route is of the order of 250 mg/kg.
B - OVERALL BEHAVIOUR AND REACTIVITIES Batches of 6 animals are observed before, then 15 minutes, 30 minutes, 1 hr., 2 hrs., 3 hrs. and 24 hrs. after administration of CRL 40883. 1) In the mouse: At the doses of 64 mg/kg, 16 mg/kg, 4 mg/kg and 1 mg/kg, CRL 40883 does not bring about any substantial changes in behaviour and reactivities. Moderate sedation is observed particularly at the dose of 128 mg/kg. 6 6 5 4987 2) In the rat: At the dose o£ 32 mg/kg, a hyporeactivity to touch and a muscular hypotonia are observed for 30 minutes; at the doses of 8 mg/kg, 2 mg/kg and 0.5 mg/kg, no particular symptoms are observed.
C - ACTION ON THE CNS CRL 40883 presents the effects of an antidepressant substance (antagonism of the hypothermias induced by apomorphine, reserp'me or oxotremorine) as well as a potentialization of the amphetaminic stereotypies.
Furthermore, at the doses of 16 mg/kg and 64 mg/kg, CRL 40883 brings about a considerable reduction in the number of fights in the groups of mice, according to the intergroup aggressiveness method.
Claims (9)
1. 7 754987 i. An N-(benzhydrylsulfinylall (wherein R represents a Cj-C^-alkyl group), and b) add addition salts thereof.
2. An N-(benzhydrylsulfinylalkyl)-amine derivative of formula I according to Claim I, wherein R is CH^, CH^CH^, i-C^H^ or t-C^H^.
3. N-[2-(benzhydrylsulfinyl)-ethyl]-methylamine or an acid addition salt thereof. ¢.
4.A therapeutical composition comprising, in association with a physiologically acceptable excipient, a pharmaceutically effective amount of an N-(benzhydrylsulfinylalkyl)-amine derivative according to Claim 1.
5. A method for preparing an N-(benzhydrylsulfinylethy()-amine derivative according to claim 1, said method comprising successively a) reacting in water in the presence of a base selected from NaOH and KOH, diphenylmethanethiol of the formula (c6h5)2 CH- SH (II) with a 2-bromoethylamine of the formula BrCH2CH2NHR (III) (wherein R is as defined in claim 1), under refluxing for at least 1 hour, using from 1 to 1.2 mole of III for 1 mole of II, so as to obtain a benzhydrylthioethylamine of the formula (C6H5)2CH " S ~ CH2CH2 " HHR lIV) then, b) oxidizing said benzhydrylthioethylamine thus obtained with 11^2 at 110-130 volumes in acetic acid, at a temperature of 40-45°C for 1 hour.
6. An N-benzhydrylsulfinylalky1-amine derivative of the formula I given and defined in claim 1 or an acid addition salt thereof, which is any one of those specifically hereinbefore mentioned, with the exception of the compound claimed in claim 3.
7. A therapeutical composition according to claim 4, substantially as hereinbefore described.
8. A method for preparing an N-benzhydrylsulfinylalky 1-amine derivative of the formula I given and defined in claim 1 or an acid addition salt thereof, substantially as hereinbefore described with particular reference to the accompanying Preparatory Examples.
9. An N-benzhydrylsulfinylalky1-amine derivative of the formula X given and defined in claim 1 or an acid addition salt thereof, whenever prepared by a method claimed in claim 5 or 8. F. R. KELLY & CO. AGENTS FOR THE APPLICANTS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8209804A FR2528040A1 (en) | 1982-06-04 | 1982-06-04 | BENZHYDRYLSULFINYLETHYLAMINES, PREPARATION METHOD AND THERAPEUTIC USE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE831249L IE831249L (en) | 1983-12-04 |
| IE54987B1 true IE54987B1 (en) | 1990-04-11 |
Family
ID=9274665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1249/83A IE54987B1 (en) | 1982-06-04 | 1983-05-26 | Benzhydrylsulfinylethylamine derivatives |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0097546B1 (en) |
| JP (1) | JPS591457A (en) |
| AT (1) | ATE15796T1 (en) |
| CA (1) | CA1215393A (en) |
| DE (1) | DE3360881D1 (en) |
| DK (1) | DK160090C (en) |
| ES (1) | ES8403447A1 (en) |
| FR (1) | FR2528040A1 (en) |
| IE (1) | IE54987B1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4518637B2 (en) * | 2000-07-07 | 2010-08-04 | 住友精化株式会社 | Process for producing 2- (methylsulfonyl) ethylamine |
| US7314875B2 (en) | 2004-04-13 | 2008-01-01 | Cephalon, Inc. | Tricyclic aromatic and bis-phenyl sulfinyl derivatives |
| WO2014138518A2 (en) | 2013-03-08 | 2014-09-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Potent and selective inhibitors of monoamine transporters; method of making; and use thereof |
| US11365195B2 (en) | 2017-11-13 | 2022-06-21 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Atypical inhibitors of monoamine transporters; method of making; and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1520812A (en) * | 1975-10-02 | 1978-08-09 | Lafon Labor | Benzhydrylsulphinyl derivatives |
-
1982
- 1982-06-04 FR FR8209804A patent/FR2528040A1/en active Granted
-
1983
- 1983-05-26 AT AT83401048T patent/ATE15796T1/en not_active IP Right Cessation
- 1983-05-26 DE DE8383401048T patent/DE3360881D1/en not_active Expired
- 1983-05-26 IE IE1249/83A patent/IE54987B1/en not_active IP Right Cessation
- 1983-05-26 EP EP83401048A patent/EP0097546B1/en not_active Expired
- 1983-05-31 CA CA000429260A patent/CA1215393A/en not_active Expired
- 1983-06-03 DK DK253483A patent/DK160090C/en not_active IP Right Cessation
- 1983-06-03 ES ES522983A patent/ES8403447A1/en not_active Expired
- 1983-06-04 JP JP58098796A patent/JPS591457A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS591457A (en) | 1984-01-06 |
| CA1215393A (en) | 1986-12-16 |
| DE3360881D1 (en) | 1985-10-31 |
| DK253483A (en) | 1983-12-05 |
| FR2528040A1 (en) | 1983-12-09 |
| EP0097546B1 (en) | 1985-09-25 |
| ATE15796T1 (en) | 1985-10-15 |
| DK160090B (en) | 1991-01-28 |
| ES522983A0 (en) | 1984-03-16 |
| ES8403447A1 (en) | 1984-03-16 |
| DK253483D0 (en) | 1983-06-03 |
| EP0097546A1 (en) | 1984-01-04 |
| FR2528040B1 (en) | 1984-12-28 |
| IE831249L (en) | 1983-12-04 |
| DK160090C (en) | 1991-06-24 |
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