CA1296021C - 2-(benzhydrylsulfonyl)acetamide, a process for its preparation and itstherapeutic use - Google Patents
2-(benzhydrylsulfonyl)acetamide, a process for its preparation and itstherapeutic useInfo
- Publication number
- CA1296021C CA1296021C CA000559871A CA559871A CA1296021C CA 1296021 C CA1296021 C CA 1296021C CA 000559871 A CA000559871 A CA 000559871A CA 559871 A CA559871 A CA 559871A CA 1296021 C CA1296021 C CA 1296021C
- Authority
- CA
- Canada
- Prior art keywords
- acetamide
- benzhydrylsulfonyl
- preparation
- compound
- itstherapeutic
- 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
- ZESNOWZYHYRSRY-UHFFFAOYSA-N 2-benzhydrylsulfonylacetamide Chemical compound C=1C=CC=CC=1C(S(=O)(=O)CC(=O)N)C1=CC=CC=C1 ZESNOWZYHYRSRY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 5
- HCRQRIFRHGPWBH-UHFFFAOYSA-N 2-benzhydrylsulfanylacetamide Chemical compound C=1C=CC=CC=1C(SCC(=O)N)C1=CC=CC=C1 HCRQRIFRHGPWBH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 206010000087 Abdominal pain upper Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 208000000059 Dyspnea Diseases 0.000 description 3
- 206010013975 Dyspnoeas Diseases 0.000 description 3
- 208000006550 Mydriasis Diseases 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000007379 Muscle Hypotonia Diseases 0.000 description 2
- 208000027419 Muscular hypotonia Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- SRCCYSUDRUXYQJ-UHFFFAOYSA-N 2-benzhydrylsulfanylacetyl chloride Chemical compound C=1C=CC=CC=1C(SCC(=O)Cl)C1=CC=CC=C1 SRCCYSUDRUXYQJ-UHFFFAOYSA-N 0.000 description 1
- ZNTZDLKAWLXDKF-UHFFFAOYSA-N 3,3-diphenylpropanethioyl chloride Chemical compound C=1C=CC=CC=1C(CC(=S)Cl)C1=CC=CC=C1 ZNTZDLKAWLXDKF-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The subject of the present invention is 2-(benzhydrylsulfonyl) acetamide, which is a compound of the Formula I:
- SO 2 - CH2 - CONH2 I
This compound exhibits an activity on the central nervous system and may be used in therapy. There is also disclosed a process for the preparation and the usage of this compound as an active ingredient in therapeutic compositions.
The subject of the present invention is 2-(benzhydrylsulfonyl) acetamide, which is a compound of the Formula I:
- SO 2 - CH2 - CONH2 I
This compound exhibits an activity on the central nervous system and may be used in therapy. There is also disclosed a process for the preparation and the usage of this compound as an active ingredient in therapeutic compositions.
Description
~6~ 2~
The present invention ralates to 2-(benzhydrylsulfonyl) acetamide, a process for its preparation and its therapeutic use.
Thus, the subject of the present invention is 2 (benzhydryl-sulfonyl) acetamide which is a compound of f~rmula:
~\
~Y
The applicant has di~covered that this compound exhibitQ an activity on the central nervous system and may be used in therapy.
The present invention ralates to 2-(benzhydrylsulfonyl) acetamide, a process for its preparation and its therapeutic use.
Thus, the subject of the present invention is 2 (benzhydryl-sulfonyl) acetamide which is a compound of f~rmula:
~\
~Y
The applicant has di~covered that this compound exhibitQ an activity on the central nervous system and may be used in therapy.
2-(benzhydrylsulfonyl) acetamide can be prepared by oxlda~ion.
in particular by hydrogen peroxide, from 2-(benzhydrylthio) acetamide~
the latter itself being prepared by reaction of ammonia with 2-(benzhydrylthio) acetyl chloride.
Therapeutic compositions containing 2-(benzhydrylsulfonyl) acetamide as active ingredient are also a subject of the present invention.
The following example illustrates the preparation of the compound:
a) Preparation of 2-(benzhydry~ o) acetamide 21 g (0.076 mole) of benzhydrylthioacetyl chloride dissolved in 100 ml of methylene chloride are added drop-wise with stirring to 40 ml of ammonia and 40 ml of water. After being stirred for 1 hour, the organic pha~e i~ separated, washed with water and dried over Na2S04. The solvent iq e~aporated in a vacuum, the residue is crystallized from isopropyl ether and recrystallized from ethyl acetate. The compound is obtained in a yield of 45~.
It is a white powder, soluble in alcohols, acetone, ethyl acetate; insoluble in water, isopropyl ether. It melts at 107-108C.
b) Preparation of 2-(benzhydrylsulfonYl) acetamide (Code ~o. CRL 41 056) 12.85 g (0.05 mole) of 2-(benzhydrylthio) acetamide dissolved In 50 m} of acetic acid are oxidized by the drop-wise addition of 15 ml (0.15 mole) of 110 Yolumes strength hydrogen peroxide bet~een 20 and 30C.
After being ~tirred for 5 hours9 the mixture is left ~o stand for 48 hour3.
The sulfone is filtered off, washed with water, dried and recry~tallized from ethanol.
~ : .
~.. ~, .
~z~
The compound is obtained in an overall yield of 36%.
It exists in the form of white needles, soluble in alcohols, acetone; slightly soluble in chloroform, ethyl acetate; insoluble in ethyl ether, water. It melts at 194C.
The results of the pharmacological studies on the compound (CRL 41 056) demonstrating its properties will be given below.
A suspension of CRL 41 056 in a solution of gum arabic was administered by the intraperitoneal route in a volume of 20 ml/kg to the mouse (male, NMRI, Evic Ceba) and 5 ml/kg to the rat (male, CDl, SPRAGUE DAWLEY, Charles).
I - Pretoxicity (3 mice per dose) - At doses of 64,_128 and 256 mg/kg appearance of stomach cramps - At a dose of 512 mg/kg: stomach cramps, dyspnea.
- At a dose of 1024 mg/kg: stomach cramps, dyspnea, sedation, no deaths.
II - General behaviour and reactivity Groups of 3 rats were observered before and then at 15 mn, ;~ 30 mn, 1 h, 2 h, 3 h and 24 h after administration of CRL 41 056.
4 mg/kg: hypo-reactivity on being touched (30 mn) 25- 16 mg/kg: hypo-reactivity on being touched (30 mn) : mydriasis for 2 to 3 hours - 64 mg/kg: hypo-reactivity on being touched (30 to 60 mn) :: :
: muscular hypotonia (15 mn) : mydriasis for 1 hour - 256 mg/kg: hypo-reactivity on being touched and muscular hypotonia for 30 mn.
: mydriasis for 1 to 3 hours : dyspnea for 2 hours.
~:
q~
III - Action on spontaneous motility A half-hour after being given CRL 41 056, the mice (6 per dose, 12 controls) are placed in an actimeter where their motility is recorded for 30 minutes.
At doses of 12~ and 512 mg/kg, CRL 41 056 brings about a diminution in spontaneous motor activity.
Conclusion CRL 41 056 shows a sedative effect associated with hypo-motility and hypo-reactivity.
CRL 41 056 has proved to be a good sedative in man when two tablets each containing 100 mg are taken per day.
The therapeutic compositions according to the invention may be administered to man or animals by the oral and parentera7 routes.
They may be available in the form of solid or semi-solid preparations. As examples may be cited tablets, capsules, suppositories as well as delayed-release forms.
In these compositions, the active ingredient is usually mixed with one or more of the pharmaceutically acceptable excipients usually used and well-known to the specialist.
The quantity of active ingredient administered obviously depends on the patient who is being treated, the route of administration and the severity of the disease.
in particular by hydrogen peroxide, from 2-(benzhydrylthio) acetamide~
the latter itself being prepared by reaction of ammonia with 2-(benzhydrylthio) acetyl chloride.
Therapeutic compositions containing 2-(benzhydrylsulfonyl) acetamide as active ingredient are also a subject of the present invention.
The following example illustrates the preparation of the compound:
a) Preparation of 2-(benzhydry~ o) acetamide 21 g (0.076 mole) of benzhydrylthioacetyl chloride dissolved in 100 ml of methylene chloride are added drop-wise with stirring to 40 ml of ammonia and 40 ml of water. After being stirred for 1 hour, the organic pha~e i~ separated, washed with water and dried over Na2S04. The solvent iq e~aporated in a vacuum, the residue is crystallized from isopropyl ether and recrystallized from ethyl acetate. The compound is obtained in a yield of 45~.
It is a white powder, soluble in alcohols, acetone, ethyl acetate; insoluble in water, isopropyl ether. It melts at 107-108C.
b) Preparation of 2-(benzhydrylsulfonYl) acetamide (Code ~o. CRL 41 056) 12.85 g (0.05 mole) of 2-(benzhydrylthio) acetamide dissolved In 50 m} of acetic acid are oxidized by the drop-wise addition of 15 ml (0.15 mole) of 110 Yolumes strength hydrogen peroxide bet~een 20 and 30C.
After being ~tirred for 5 hours9 the mixture is left ~o stand for 48 hour3.
The sulfone is filtered off, washed with water, dried and recry~tallized from ethanol.
~ : .
~.. ~, .
~z~
The compound is obtained in an overall yield of 36%.
It exists in the form of white needles, soluble in alcohols, acetone; slightly soluble in chloroform, ethyl acetate; insoluble in ethyl ether, water. It melts at 194C.
The results of the pharmacological studies on the compound (CRL 41 056) demonstrating its properties will be given below.
A suspension of CRL 41 056 in a solution of gum arabic was administered by the intraperitoneal route in a volume of 20 ml/kg to the mouse (male, NMRI, Evic Ceba) and 5 ml/kg to the rat (male, CDl, SPRAGUE DAWLEY, Charles).
I - Pretoxicity (3 mice per dose) - At doses of 64,_128 and 256 mg/kg appearance of stomach cramps - At a dose of 512 mg/kg: stomach cramps, dyspnea.
- At a dose of 1024 mg/kg: stomach cramps, dyspnea, sedation, no deaths.
II - General behaviour and reactivity Groups of 3 rats were observered before and then at 15 mn, ;~ 30 mn, 1 h, 2 h, 3 h and 24 h after administration of CRL 41 056.
4 mg/kg: hypo-reactivity on being touched (30 mn) 25- 16 mg/kg: hypo-reactivity on being touched (30 mn) : mydriasis for 2 to 3 hours - 64 mg/kg: hypo-reactivity on being touched (30 to 60 mn) :: :
: muscular hypotonia (15 mn) : mydriasis for 1 hour - 256 mg/kg: hypo-reactivity on being touched and muscular hypotonia for 30 mn.
: mydriasis for 1 to 3 hours : dyspnea for 2 hours.
~:
q~
III - Action on spontaneous motility A half-hour after being given CRL 41 056, the mice (6 per dose, 12 controls) are placed in an actimeter where their motility is recorded for 30 minutes.
At doses of 12~ and 512 mg/kg, CRL 41 056 brings about a diminution in spontaneous motor activity.
Conclusion CRL 41 056 shows a sedative effect associated with hypo-motility and hypo-reactivity.
CRL 41 056 has proved to be a good sedative in man when two tablets each containing 100 mg are taken per day.
The therapeutic compositions according to the invention may be administered to man or animals by the oral and parentera7 routes.
They may be available in the form of solid or semi-solid preparations. As examples may be cited tablets, capsules, suppositories as well as delayed-release forms.
In these compositions, the active ingredient is usually mixed with one or more of the pharmaceutically acceptable excipients usually used and well-known to the specialist.
The quantity of active ingredient administered obviously depends on the patient who is being treated, the route of administration and the severity of the disease.
Claims (3)
1. 2-(benzhydrylsulfonyl) acetamide.
2. Process for the preparation of 2-(benz-hydrylsulfonyl) acetamide, comprising the oxidation of 2-(benzhydrylthio) acetamide.
3. Therapeutic composition comprising a compound according to Claim 1 as active ingredient and a pharmaceutically acceptable carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8702586 | 1987-02-26 | ||
| FR8702586A FR2611709B1 (en) | 1987-02-26 | 1987-02-26 | 2- (BENZHYDRYLSULFONYL) ACETAMIDE, ITS PREPARATION PROCESS AND ITS APPLICATION IN THERAPEUTICS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1296021C true CA1296021C (en) | 1992-02-18 |
Family
ID=9348363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000559871A Expired - Lifetime CA1296021C (en) | 1987-02-26 | 1988-02-25 | 2-(benzhydrylsulfonyl)acetamide, a process for its preparation and itstherapeutic use |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0283362B1 (en) |
| JP (1) | JPH0825989B2 (en) |
| AT (1) | ATE65248T1 (en) |
| CA (1) | CA1296021C (en) |
| DE (1) | DE3863665D1 (en) |
| ES (1) | ES2040362T3 (en) |
| FR (1) | FR2611709B1 (en) |
| GR (1) | GR3002328T3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8048222B2 (en) | 2000-07-27 | 2011-11-01 | Teva Pharmaceutical Industries, Ltd. | Highly pure modafinil |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05008088A (en) | 2003-02-24 | 2005-09-21 | Mallinckrodt Inc | Process for preparing benzhydrylthioacetamide. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1584462A (en) * | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
-
1987
- 1987-02-26 FR FR8702586A patent/FR2611709B1/en not_active Expired
-
1988
- 1988-02-24 DE DE8888400432T patent/DE3863665D1/en not_active Expired - Lifetime
- 1988-02-24 ES ES88400432T patent/ES2040362T3/en not_active Expired - Lifetime
- 1988-02-24 EP EP88400432A patent/EP0283362B1/en not_active Expired - Lifetime
- 1988-02-24 AT AT88400432T patent/ATE65248T1/en not_active IP Right Cessation
- 1988-02-25 JP JP63043267A patent/JPH0825989B2/en not_active Expired - Lifetime
- 1988-02-25 CA CA000559871A patent/CA1296021C/en not_active Expired - Lifetime
-
1991
- 1991-07-18 GR GR91400957T patent/GR3002328T3/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8048222B2 (en) | 2000-07-27 | 2011-11-01 | Teva Pharmaceutical Industries, Ltd. | Highly pure modafinil |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2611709B1 (en) | 1989-06-09 |
| JPS63301856A (en) | 1988-12-08 |
| GR3002328T3 (en) | 1992-12-30 |
| JPH0825989B2 (en) | 1996-03-13 |
| ATE65248T1 (en) | 1991-08-15 |
| EP0283362A1 (en) | 1988-09-21 |
| EP0283362B1 (en) | 1991-07-17 |
| ES2040362T3 (en) | 1995-04-01 |
| DE3863665D1 (en) | 1991-08-22 |
| FR2611709A1 (en) | 1988-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |