GB2184122A - N,n-dimethyl-1-1-(4-chlorophenyl)cyclobutyl-3-methylbutylamine saltt - Google Patents
N,n-dimethyl-1-1-(4-chlorophenyl)cyclobutyl-3-methylbutylamine saltt Download PDFInfo
- Publication number
- GB2184122A GB2184122A GB08629568A GB8629568A GB2184122A GB 2184122 A GB2184122 A GB 2184122A GB 08629568 A GB08629568 A GB 08629568A GB 8629568 A GB8629568 A GB 8629568A GB 2184122 A GB2184122 A GB 2184122A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorophenyl
- dimethyl
- cyclobutyl
- water
- methylbutylamine
- 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
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
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
Description
SPECIFICATION
Therapeutic compound
The present invention relates to N, N-dimethyl-1- [1- 4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride which is useful in the treatment of depression.
British Patent Specification 2098602 describes preparative methods which would be suitable for the preparation of the above compound. The present applicants have found that different samples of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride prepared by methods described in the above identified patent application have variable amounts of water contained therein and that these samples are hygroscopic. It is undesirable that hygroscopic materials are used in the preparation of medicines because of the difficulties inherent in the handling of hygroscopic materials. In the preparation of medicines it is essential that a consistent weight of active ingredient is included in each dosage form and it is difficult to achieve such consistency with active ingredients which are absorbing water from the environment. It has now been found that if N, I-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride is prepared in the form of a monohydrate a non-hygroscopic product is obtained which is suitable for the preparation of capsules, tablets and other pharmaceutical dosage forms. The present invention therefore comprises N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbuty- lamine hydrochloride monohydrate, methods for its preparation, pharmaceutical ~ containing it and the use of those pharmaceutical compositions in the treatment of depression.
N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate may be prepared by contacting N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride with a medium consisting of or containing water. In a preferred method N, N- dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate is prepared by recrystallising N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride from water or a medium containing water, which may be a mixture of water and a water-immiscible solvent (e. g. toluene, xylene or cyclohexane) or a mixture of water and a watermiscible solvent (e. g. acetone, propan-2-ol, industrial methylated spirit, 2-ethoxyethanol, tetrahydrofuran, 1,4-dioxan, methyl acetate or 1,2-dimethoxyethane). Alternative methods to prepare N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate include (a) contacting solid N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride, preferably in finely divided form, with a gaseous medium consisting of or containing water vapour and (b) suspending N, Ndimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride in water or a water-containing medium.
N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate may also be prepared by treating N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylam- ine with hydrochloric acid or a solvent (e. g. acetone or ethanol) containing hydrochloric acid.
The present invention includes pharmaceutical compositions for use in the treatment of depression containing a therapeutically effective amount of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]- 3-methylbutylamine hydrochloride monohydrate in combination with a pharmaceutically acceptable diluent or carrier. These pharmaceutical compositions may take the form of any of the known pharmaceutical compositions for oral, rectal, parenteral or topical administration. Pharmaceutically acceptable diluent and carriers suitable for use in these compositions are well known in the art of pharmacy. The preferred pharmaceutical compositions are tablets or capsules intended for oral administration. Each tablet or capsule may contain 0.5 to 25 preferably 1 to 12.5 milligrams of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate.
The pharmaceutical compositions of the present invention may be used in the treatment of depression in humans. In such treatment a total of 0.5 to 150 preferably 1 to 50 milligrams of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate maybe administered daily in one or more doses.
The invention will now be illustrated by the following Examples which describe the preparation of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate.
The present applicants have found that N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbu- tylamine hydrochloride, which was prepared by methods described in British Patent Specification 2098602 and which is used as the starting material for Examples 1 to 11 and 14 to 16, is hygroscopic and may contain variable amounts, but less than one molar equivalent, of water.
The products of the Examples hereinafter were characterised by satisfactory elemental (C, H, N, CI) analyses and by satisfactory analysis for their water content.
When attempts are made to determine the melting point of N, N-dimethyl-1- [1- (4-chlorophenyl)- cyclobutyl]-3-methylbutylamine hydrochloride monohydrate using conventional laboratory apparatus, it is believed that the sample dehydrates as the temperature is raised and that the melting point observed is that of the dehydrated material.
N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride (0.5 g) was dissolved in boiling water (5 ml). The solution was filtered whilst hot and the filtrate cooled. The product crystallised from the cooled filtrate and was collected by filtration and dried in vacuo at ambient temperature to give N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate (m. p. 193-195.5 C).
Example 2 N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride (5 g) was dissolved in a boiling mixture of toluene (126 ml) and water (12.6 ml). The solution was filtered whilst hot and the filtrate cooled. The product crystallised from the cooled filtrate and was collected by filtration and dried in vacuo at ambient temperature to give NN-dimethyl-l- [l- (4- chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate (m. p. 194-196 C).
Example 3
N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride (10 g) was dissolved in a boiling mixture of acetone (110 ml) and water (1.2 ml). The solution was filtered whilst hot and the volume of the filtrate reduced by the removal by distillation of 80 mi of solvent. The product was collected from the cooled concentrate by filtration and dried in vacuo at ambient temperature to give N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate (m. p. 195 C).
Examples 4 to 6
A sample (1 g) of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochlo- ride which has been dehydrated in vacuo at 70 C for 7 hours was dissolved in a boiling mixture of water (0.5 ml) and an organic solvent (4.5 ml). The solution was allowed to cool to ambient temperature and then stored at 4 C for three hours. A solid was collected by filtration, washed with the organic solvent and dried in vacuo at ambient temperature for 18 hours to give N, N- dimethyl-l- [l- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate the melting point of which is given below.
Ex. Solvent Melting Point C 4 industrial methylated 195-198 (shrinks 160)
spirit 5 propan-2-ol 195-198 (shrinks 163) 6 2-ethoxyethanol 194-198 (shrinks 166)
Examples 7 to 11 A sample (1 g) of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochlo- ride which had been dehydrated in vacuo at 70 C for 7 hours was treated with an organic solvent specified below (x ml) and then water (y ml) was added. The mixture was boiled and the resulting solution allowed to cool to ambient temperature and then stored at 4 C for three hours.
In Examples 10 and 11 the solution was stored at ambient temperature for 18 hours and crystallisation initiated by reducing the volume of the solution under a stream of air. A solid was collected by filtration, washed with the organic solvent and dried in vacuo at ambient temperature for 18 hours to give N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate the melting point of which is given below.
Ex. Solvent x y Melting Point C 7 1,2-dimethoxy- 10 1 196-198 (shrinks 185)
ethane 8 xylene 15 1 196-198 (shrinks 166) 9 cyclohexane 30 2 193-197 (shrinks 160) 10 1,4-dioxan 25 1 196-199 (shrinks 160) 11 methyl acetate 25 2 197-202 Examples 12 and 13 A sample (1 g) of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine was treated with 5M hydrochloric acid (1 ml) and the mixture was dissolved in the minimum quantity of a boiling organic solvent specified below. The resulting solution was allowed to cool to ambient temperature. A solid was collected by filtration, washed with the organic solvent and dried in vacuo at ambient temperature for 18 hours to give N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]- 3-methylbutylamine hydrochloride monohydrate the melting point of which is given below.
Ex. Solvent Melting Point C 12 acetone 194-197 13 ethanol 196-201 Example 14 A sample (5 g) of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochlo- ride was heated with a mixture of toluene (30 mi) and propan-2-ol (3 ml) to 90 C and allowed to cool to 72 C. Water (0.9 ml) was added and the mixture cooled to 25 C and then placed in an ice-water bath for 30 minutes. A solid was collected by filtration, washed with cold toluene and dried by suction at ambient temperature to give N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobu- tyl]-3-methylbutylamine hydrochloride monohydrate [m. p. 193-195 C (shrinks 150-155 C)].
Example 15 A sample (24.1 g) of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride was dissolved in a boiling mixture of water (72 ml) and tetrahydrofuran (7 ml) and the mixture allowed to cool. A solid was collected by filtration and dried at 40 C to give N, N- dimethyl-l- [l- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate (m. p.
193-195 C).
Example 16 A sample (48.2 g) of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride was suspended and stirred with water (145 ml) for 24 hours at 25 C. The solid was collected by filtration and dried by suction at ambient temperature to give NN-dimethyl-l- [l- (4- chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate (m. p. 191-195.5 C).
The non-hygroscopic nature of the products prepared in the Examples hereinbefore is illustrated by the following comparative experiment. A sample of N, N-dimethyl-1- [1- (4-chlorophenyl)- cyclobutyl]-3-methylbutylamine hydrochloride was dehydrated in a vacuum oven at 60 C for 16 hours and stored in a desiccator over phosphorus pentoxide. Analysis showed that this material contained no water. When the sample was exposed to the atmosphere for one month analysis showed the water content to be approximately 3% corresponding to about 0.6 molar equivalents of water. However, when a sample of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbuty- lamine hydrochloride monohydrate was exposed to the atmosphere for five months there was no increase in water content showing that no absorption of water had occurred.
Claims (13)
- CLAIMS 1. N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate.
- 2. Pharmaceutical compositions comprising N, Ndimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-me- thylbutylamine hydrochloride monohydrate together with a pharmaceutically acceptable diluent or carrier.
- 3. N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate for use in the treatment of depression in humans.
- 4.-A process for the preparation of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbu- tylarnine hydrochloride monohydrate comprising contacting N, N-dimethyl-1- [1- 4-chlorophenyl) cy clobutyl]-3-methylbutylamine hydrochloride with a medium consisting of or containing water.
- 5. A process as claimed in claim 4 which comprises recrystallising NN-dimethyl-l- [l- (4- chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride from a medium consisting of or containing water
- 6. A process as claimed in claim 5 in which the medium containing water is a mixture of water and a water-immiscible solvent.
- 7. A process as claimed in claim 6 in which the water-immiscible solvent is toluene, xylene or cyclohexane.
- 8. A process as claimed in claim 5 in which the solvent containing water is a mixture of water and a water-miscible solvent.
- 9. A process as claimed in claim 8 in which the water-miscible solvent is acetone, propan-2ol, industrial methylated spirit, 2-ethoxyethanol, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxan or methyl acetate.
- 10. A process for the preparation of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbu- tylamine hydrochloride monohydrate as claimed in claim 4 comprising contacting solid N, N- dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride with a gaseous medium consisting of or containing water vapour.
- 11. A process for the preparation of NN-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbu- tylamine hydrochloride monohydrate as claimed in claim 4 comprising suspending N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride in water or a water-containing medium.
- 12. A process for the preparation of N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbu- tylamine hydrochloride monohydrate comprising treating N, N-dimethyl-1- [1- (4-chlorophenyl) cyclo- butyl]-3-methylbutylamine with hydrochloric acid or a solvent containing hydrochloric acid.
- 13. N, N-Dimethyl-1- [1- (4-chlorophenyl) cyclobutyl]-3-methylbutylamine hydrochloride monohydrate for use in the preparation of a medicament for the treatment of depression.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8629568A GB2184122B (en) | 1985-12-17 | 1986-12-10 | N,n-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl butylamine hydrochloride monohydrate |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB858531071A GB8531071D0 (en) | 1985-12-17 | 1985-12-17 | Therapeutic compound |
GB8629568A GB2184122B (en) | 1985-12-17 | 1986-12-10 | N,n-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl butylamine hydrochloride monohydrate |
Publications (3)
Publication Number | Publication Date |
---|---|
GB8629568D0 GB8629568D0 (en) | 1987-01-21 |
GB2184122A true GB2184122A (en) | 1987-06-17 |
GB2184122B GB2184122B (en) | 1989-10-18 |
Family
ID=26290128
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8629568A Expired GB2184122B (en) | 1985-12-17 | 1986-12-10 | N,n-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl butylamine hydrochloride monohydrate |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB2184122B (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4939175A (en) * | 1988-03-31 | 1990-07-03 | The Boots Co. Plc | Use of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine |
US5359121A (en) * | 1991-10-25 | 1994-10-25 | Ono Pharmaceutical Co., Ltd. | Glycine derivative monosodium salt tetrahydrate |
US5436272A (en) * | 1988-11-29 | 1995-07-25 | The Boots Company (Usa), Inc. | Treatment of obesity |
US6900245B2 (en) * | 2002-10-05 | 2005-05-31 | Hanmi Pharm. Co., Ltd. | Pharmaceutical composition comprising crystalline sibutramine methanesulfonate hemihydrate |
WO2006073292A1 (en) | 2005-01-06 | 2006-07-13 | Cj Corporation | Inorganic acid salts of sibutramine |
WO2012004588A2 (en) | 2010-07-06 | 2012-01-12 | Astrazeneca Ab | Therapeutic agents 976 |
WO2012064267A1 (en) | 2010-11-08 | 2012-05-18 | Albireo Ab | A pharmaceutical combination comprising an ibat inhibitor and a bile acid binder |
WO2012064266A1 (en) | 2010-11-08 | 2012-05-18 | Albireo Ab | Ibat inhibitors for the treatment of liver diseases |
WO2013011285A1 (en) | 2011-07-15 | 2013-01-24 | Astrazeneca Ab | Azetidine derivatives for treatment of melanin related disorders |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2098602A (en) * | 1981-04-06 | 1982-11-24 | Boots Co Plc | Therapeutic agents |
-
1986
- 1986-12-10 GB GB8629568A patent/GB2184122B/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2098602A (en) * | 1981-04-06 | 1982-11-24 | Boots Co Plc | Therapeutic agents |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4939175A (en) * | 1988-03-31 | 1990-07-03 | The Boots Co. Plc | Use of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine |
US5436272A (en) * | 1988-11-29 | 1995-07-25 | The Boots Company (Usa), Inc. | Treatment of obesity |
US5359121A (en) * | 1991-10-25 | 1994-10-25 | Ono Pharmaceutical Co., Ltd. | Glycine derivative monosodium salt tetrahydrate |
US6900245B2 (en) * | 2002-10-05 | 2005-05-31 | Hanmi Pharm. Co., Ltd. | Pharmaceutical composition comprising crystalline sibutramine methanesulfonate hemihydrate |
WO2006073292A1 (en) | 2005-01-06 | 2006-07-13 | Cj Corporation | Inorganic acid salts of sibutramine |
WO2012004588A2 (en) | 2010-07-06 | 2012-01-12 | Astrazeneca Ab | Therapeutic agents 976 |
WO2012064267A1 (en) | 2010-11-08 | 2012-05-18 | Albireo Ab | A pharmaceutical combination comprising an ibat inhibitor and a bile acid binder |
WO2012064266A1 (en) | 2010-11-08 | 2012-05-18 | Albireo Ab | Ibat inhibitors for the treatment of liver diseases |
EP3023102A1 (en) | 2010-11-08 | 2016-05-25 | Albireo AB | Ibat inhibitors for the treatment of liver diseases |
EP3777864A1 (en) | 2010-11-08 | 2021-02-17 | Albireo AB | Ibat inhibitors for the treatment of liver diseases |
WO2013011285A1 (en) | 2011-07-15 | 2013-01-24 | Astrazeneca Ab | Azetidine derivatives for treatment of melanin related disorders |
Also Published As
Publication number | Publication date |
---|---|
GB8629568D0 (en) | 1987-01-21 |
GB2184122B (en) | 1989-10-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5068440A (en) | Process for the manufacture of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate | |
CN1043405C (en) | Pharmaceutical agents | |
SE450830B (en) | STABLE MICROCrystalline CIS-PLATINA (II) DIAMINE DICHLORIDE AND PROCEDURE FOR ITS PREPARATION | |
UA57189C2 (en) | b-CRYSTALLINE FORM OF PERINDOPRIL TRET-BUTYLAMINE SALT, A PROCESS FOR PREPARING THEREOF AND A PHARMACEUTICAL COMPOSITION CONTAINING IT | |
GB2184122A (en) | N,n-dimethyl-1-1-(4-chlorophenyl)cyclobutyl-3-methylbutylamine saltt | |
CN102321019A (en) | The crystalline form of quinoline compound and working method thereof | |
CA2656711A1 (en) | Novel hydrate form of moxifloxacin monohydrochloride | |
EP0944612B1 (en) | N-(4-acetyl-1-piperazinyl)-4-fluorobenzamide hydrate | |
US4006159A (en) | Substituted 1,2,4-triazole carboxamides | |
EP0560136B1 (en) | Neuroprotective drug | |
EP0646586B1 (en) | 2-aminoethanesulfonic acid/zinc complex compound | |
US4089970A (en) | Method of inhibiting platelet aggregation | |
US3131197A (en) | 5-(3, 4-carbonyldioxyphenyl)-3-isopropyl-2-oxazolidone | |
US2917536A (en) | Aminoalkyldicyclopropylalkynols | |
JPH032183A (en) | Bisbenzylisoquinoline derivative | |
CN100999521B (en) | Crystal anti-choline medicine thiatropic bromoammonium | |
CN114478287A (en) | Aspirin-lysine crystal form, preparation method and application | |
RU2162695C1 (en) | Method of preparing ondansetron hydrochloride dihydrate, substance and pharmaceutical preparation | |
US4007198A (en) | Substituted 1,2,4-triazole carboxamide | |
AU4867799A (en) | Injectable sodium acetylsalicylate composition and method | |
EP0301465A1 (en) | Crystalline monohydrate of sodium N-(1H-tetrazol-5-yl)-1-phenoxy-4H-quinolizin-4-one-3-carboxamide | |
MXPA99005427A (en) | N-(4-acetyl-1-piperazinyl)-4-fluorobenzamide hydrate | |
TH4445A (en) | Pure optical compounds and their preparation processes |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
773I | Case decided by the comptroller (sect. 73(2)/1977) |