GB804492A - Aminopyrine, caffeine or quinine hydrochloride inclusion compounds - Google Patents
Aminopyrine, caffeine or quinine hydrochloride inclusion compoundsInfo
- Publication number
- GB804492A GB804492A GB11890/55A GB1189055A GB804492A GB 804492 A GB804492 A GB 804492A GB 11890/55 A GB11890/55 A GB 11890/55A GB 1189055 A GB1189055 A GB 1189055A GB 804492 A GB804492 A GB 804492A
- Authority
- GB
- United Kingdom
- Prior art keywords
- weight
- urea
- aminopyrine
- parts
- caffeine
- 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
Links
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 title abstract 18
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 title abstract 13
- 229960000212 aminophenazone Drugs 0.000 title abstract 11
- 150000001875 compounds Chemical class 0.000 title abstract 10
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 title abstract 9
- 229960001948 caffeine Drugs 0.000 title abstract 9
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 title abstract 9
- 239000001096 (4-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol hydrochloride Substances 0.000 title abstract 7
- NNKXWRRDHYTHFP-HZQSTTLBSA-N (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydron;dichloride Chemical compound Cl.Cl.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 NNKXWRRDHYTHFP-HZQSTTLBSA-N 0.000 title abstract 7
- 229960001811 quinine hydrochloride Drugs 0.000 title abstract 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 8
- 239000004202 carbamide Substances 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- 238000002844 melting Methods 0.000 abstract 4
- 230000008018 melting Effects 0.000 abstract 4
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 abstract 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 3
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 abstract 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl methanes Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000155 melt Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 2
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical class CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 abstract 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 abstract 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000014593 oils and fats Nutrition 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises a water-soluble inclusion compound obtained by heating aminopyrine (4 - dimethylamino - 1,5 - dimethyl - 2-phenyl-3-pyrazolone), caffeine or quinine hydrochloride with at least the stoichiometric amount of at least one carbamic acid alkyl ester and not more than 30 per cent, calculated on the weight of said ester, of an alkyl derivative of urea, and by heating aminopyrine or caffeine with at least the stoichiometric amount of at least one carbamic acid alkyl ester, and the preparation thereof by the said method. The addition compounds may be prepared by introducing the aminopyrine, caffeine or quinine hydrochloride into a melt of the carbamic acid ester, with or without the alkyl derivative of urea, and heating the mixture to 60-70 DEG C. The resulting melt may be solidified, dissolved and spray dried to form a powder. At least two of the compounds aminopyrine, caffeine and quinine hydrochloride may be introduced into the melt. The molar ratio of the aminopyrine, caffeine or quinine hydrochloride and the said complex-forming compounds may be adjusted to about 1 : 2. The above process may also be carried out by mixing an aqueous concentrated solution of the aminopyrine, caffeine or quinine hydrochloride with an aqueous concentrated solution of the carbamic acid ester, with or without the alkyl derivative of urea, and either substantially removing all the water under reduced pressure and heating the resulting mixture to 60 DEG to 70 DEG C., or substantially removing all the water at a temperature of about 60 DEG to 70 DEG C. Suitable alkyl methanes are methyl, ethyl and trichloroethyl methanes, and suitable alkyl derivatives of urea are monomethyl urea and sym. dimethyl urea. In the examples: (1) an inclusion compound is formed from ethyl methane and aminopyrine in a mol. ratio of 2 : 1 and has a melting point of 53 DEG C., and a solubility of 1 gm. in 1.5 cc. of water at 20 DEG C. and of 1 gm. in 1 cc. of water at 55 DEG C.; similar results are obtained if up to 30 per cent, e.g. from 5 to 30 per cent, by weight of the ethyl methane is replaced by an alkyl urea, e.g. a methyl urea; (2) an inclusion compound is prepared containing 230 parts by weight of aminopyrine, 40 parts by weight of caffeine and 178 parts by weight of methyl methane and has a melting point of 60 DEG C. and a solubility of 1 gm. in 1.5 cc. of water at 20 DEG C.; (3) an inclusion compound is prepared containing 60 parts by weight of quinine hydrochloride, 37 parts by weight of methyl methane and 3 parts by weight of ethyl urea (or N,N1-dimethyl urea) and has a melting point of 45 DEG C. and a solubility of 1 gm. in 2 gm. of water at about 35-40 DEG C.; and (4) an inclusion compound is prepared containing 49 parts by weight of ethyl methane, 3 parts by weight of N,N1-dimethyl urea, 10 parts by weight of caffeine and 38 parts by weight of aminopyrine and has a melting point of 55-56 DEG C. and a solubility of 1 part in 2 parts of water at about 35-40 DEG C.ALSO:Solutions having an antipyretic effect are prepared by dissolving in water, oils or fats the inclusion compound obtained by heating aminopyrine (4 - dimethylamino - 1,5 - dimethyl - 2-phenyl - 3 - pyrazolone) with at least the stoichiometric amount of at least one carbamic acid alkyl ester with or without not more than 30 per cent, calculated on the weight of said ester, of an alkyl derivative of urea. The solutions in oils and fats may be incorporated into suppositories.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11890/55A GB804492A (en) | 1955-04-25 | 1955-04-25 | Aminopyrine, caffeine or quinine hydrochloride inclusion compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11890/55A GB804492A (en) | 1955-04-25 | 1955-04-25 | Aminopyrine, caffeine or quinine hydrochloride inclusion compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB804492A true GB804492A (en) | 1958-11-19 |
Family
ID=11316954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11890/55A Expired GB804492A (en) | 1955-04-25 | 1955-04-25 | Aminopyrine, caffeine or quinine hydrochloride inclusion compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB804492A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2379283A1 (en) * | 1977-02-05 | 1978-09-01 | Henkel Kgaa | COSMETIC PRODUCTS CONTAINING MOISTURIZING AGENTS FOR THE SKIN |
| EP0006724A1 (en) * | 1978-06-16 | 1980-01-09 | Phares Pharmaceutical Research N.V. | Pharmaceutical compositions containing urea |
-
1955
- 1955-04-25 GB GB11890/55A patent/GB804492A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2379283A1 (en) * | 1977-02-05 | 1978-09-01 | Henkel Kgaa | COSMETIC PRODUCTS CONTAINING MOISTURIZING AGENTS FOR THE SKIN |
| EP0006724A1 (en) * | 1978-06-16 | 1980-01-09 | Phares Pharmaceutical Research N.V. | Pharmaceutical compositions containing urea |
| USRE32161E (en) * | 1978-06-16 | 1986-05-27 | Phares Pharmecutical Research N.V. | Pharmaceutical compositions containing urea |
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