US3400203A - Treatment of parkinsonism in humans with nu, nu-diphenyl carbamates of alkylaminoalkanols - Google Patents
Treatment of parkinsonism in humans with nu, nu-diphenyl carbamates of alkylaminoalkanols Download PDFInfo
- Publication number
- US3400203A US3400203A US456808A US45680865A US3400203A US 3400203 A US3400203 A US 3400203A US 456808 A US456808 A US 456808A US 45680865 A US45680865 A US 45680865A US 3400203 A US3400203 A US 3400203A
- Authority
- US
- United States
- Prior art keywords
- parkinsonism
- treatment
- humans
- carbamates
- alkylaminoalkanols
- 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 - Lifetime
Links
- 208000027089 Parkinsonian disease Diseases 0.000 title description 9
- 206010034010 Parkinsonism Diseases 0.000 title description 9
- 239000004305 biphenyl Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 8
- 230000001078 anti-cholinergic effect Effects 0.000 description 7
- 206010044565 Tremor Diseases 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- 229930003347 Atropine Natural products 0.000 description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000006550 Mydriasis Diseases 0.000 description 3
- 208000005392 Spasm Diseases 0.000 description 3
- 239000000939 antiparkinson agent Substances 0.000 description 3
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
- 229960000396 atropine Drugs 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- -1 diphenyl carbamates Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- JGOAIQNSOGZNBX-UHFFFAOYSA-N 2,2-diphenylacetic acid 2-(diethylamino)ethyl ester Chemical compound C=1C=CC=CC=1C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 JGOAIQNSOGZNBX-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 229960004512 adiphenine Drugs 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000648 anti-parkinson Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 230000001410 anti-tremor Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960003941 orphenadrine Drugs 0.000 description 2
- QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 210000001747 pupil Anatomy 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000027776 Extrapyramidal disease Diseases 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KXEMQEGRZWUKJS-UHFFFAOYSA-N Raufloridine Natural products COC1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
- 206010044684 Trismus Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940035678 anti-parkinson drug Drugs 0.000 description 1
- 230000003594 anti-tremorine Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000002360 preparation method Methods 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
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229960001032 trihexyphenidyl Drugs 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Definitions
- Thls ⁇ m/entlon relates to a methPd of treatlng Parkm each of the following carbamates of the above listed sonism in humans and more particularly relates to the alkylammoalkanols;
- a high figure indicates low mydriasis (undesired side effect).
- a high figure is R2 an expression for high antitremor activity combined with wherein R and R are the same or difierent groups sea low undesired side effect.
- R with orphenadrin further demonstrates that in this field and R are phenyl, R and R are methyl or ethyl and structural resemblance does not enable prediction of a 3 specific kind of biological activity.
- R phenyl
- R and R are methyl or ethyl and structural resemblance does not enable prediction of a 3 specific kind of biological activity.
- its lower homologue containing two methyl groups instead of the two ethyls of SD-25, is a particularly effective antitremorine agent.
- the compound SD-25 is known in the literature approximately since 50 years and its local anesthetic effect and other pharamadocynamic properties have been described. Sekera and Vrba (Arc. Int., Pharmacodyn, 125, 316, 1960) state that their S-25 (identical with our SD-25) possesses 0.5-1 times the anticholinergic action of the well known spasmolytic agent Trasentine.
- Trasentine is a mainly musculotropically acting, ie a papaverinelike antispasmodic; it is evaluated in general against BaCI -induced spasms.
- the acid when isolating any of the compounds of Formula I in the form of an acid addition salt, the acid is preferably selected so as to contain an anion which is non-toxic and pharmacologically acceptable at least in usual therapeutic doses.
- Representative acid addition salts are hydrochlorides, hydrobromides, sulphates, phosphates, nitrates, acetates, lactates, maleates, citrates, tartrates and bitart-rates, succinates, oxalates, methanesulphonates and ethanesulphonates.
- Other acid addition salts are likewise suitable and may be employed if desired.
- SD- [gamm a- (N-methyl piperazino) -propyl] -phenothiazin- 2-sulfonic acid dimethylamide (thioperazin) are administered to patients (medicamental parkinsonism).
- SD- can be administered either together with the neuroleptic agent, afterwards or even before.
- SD-25 is well tolerated and no deleterious effects have been observed, even when the drug was given for more than one year.
- the patients do not complain of dryness of the mouth or other side effects, which frequently are observed when other antiparkinson remedies are administered.
- SD-25 can be given perorally and parenterally (intravenously or intramuscularly) in average doses of 15 to 50 mg., 2-4 times p.d. It is possible to inject it i.v. re-
- a 1-3%, preferably 2.5% aqueous solution, containing 25 mg. of SD-25 per ml. is generally used.
- the optimal dose is individually different and can be ascertained by the physician for singular cases.
- compositions used in the present invention can be brought into a unit dosage form by any suitable technique known to the man skilled in the art.
- a typical example of a method to prepare tablets containing the preferred 2-diethylaminoethyl-N-diphenylcarbamate will be given below: p I
- any other suitable carriers such as talc, mannose, corn starch, magnesium stearate, etc.
- a method of treating parkinsonism in human comprising administering to said humans afflicted with parkinsonism an effective amount of a compound selected from the group consisting of compounds having the following formula and pharmaceutically acceptable acid addition salts thereof wherein R and R are phenyl, R is lower alkylene and R and R independently are lower'alkyl.
- R and R are independently selected from the group consisting of methyl and ethyl.
- a method according to claim'4 wherein the compound is administered 2-4 times per day in a dosage unit between about 15 and 50 mg. of the compound.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH370961A CH405266A (de) | 1961-03-29 | 1961-03-29 | Verfahren zur Herstellung von als Antiparkinsonmittel verwendbaren Verbindungen |
| US18335662A | 1962-03-29 | 1962-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3400203A true US3400203A (en) | 1968-09-03 |
Family
ID=55539354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US456808A Expired - Lifetime US3400203A (en) | 1961-03-29 | 1965-05-18 | Treatment of parkinsonism in humans with nu, nu-diphenyl carbamates of alkylaminoalkanols |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3400203A (enExample) |
| BE (1) | BE630069A (enExample) |
| CH (1) | CH405266A (enExample) |
| FR (1) | FR2704M (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996008468A1 (en) * | 1994-09-14 | 1996-03-21 | H. Lundbeck A/S | Carbamoyloxy amine compounds |
-
1961
- 1961-03-29 CH CH370961A patent/CH405266A/de unknown
-
1963
- 1963-03-26 BE BE630069A patent/BE630069A/fr unknown
- 1963-03-29 FR FR929707A patent/FR2704M/fr not_active Expired
-
1965
- 1965-05-18 US US456808A patent/US3400203A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2704M (enExample) | 1964-09-04 |
| BE630069A (fr) | 1963-07-15 |
| CH405266A (de) | 1966-01-15 |
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