DE2236317B2 - Pharmazeutisches Präparat - Google Patents
Pharmazeutisches PräparatInfo
- Publication number
- DE2236317B2 DE2236317B2 DE2236317A DE2236317A DE2236317B2 DE 2236317 B2 DE2236317 B2 DE 2236317B2 DE 2236317 A DE2236317 A DE 2236317A DE 2236317 A DE2236317 A DE 2236317A DE 2236317 B2 DE2236317 B2 DE 2236317B2
- Authority
- DE
- Germany
- Prior art keywords
- aminophenazone
- butyl
- phenyl
- dioxo
- salt
- 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.)
- Pending
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 2
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 claims description 19
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 18
- 229960000212 aminophenazone Drugs 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 229960002895 phenylbutazone Drugs 0.000 claims description 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 4
- 229960004194 lidocaine Drugs 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- -1 α-diethylaminoacetyl - Chemical class 0.000 claims description 4
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- YFAOAESGVDKXPK-UHFFFAOYSA-N 4-butylpyrazolidine-3,5-dione Chemical compound CCCCC1C(=O)NNC1=O YFAOAESGVDKXPK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000000552 rheumatic effect Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- KOEIXVZMTIOQMJ-UHFFFAOYSA-N 1-butylpyrazolidine-3,5-dione Chemical class CCCCN1NC(=O)CC1=O KOEIXVZMTIOQMJ-UHFFFAOYSA-N 0.000 claims 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 claims 1
- NDSRBOXPULNFLZ-UHFFFAOYSA-N 3-benzyl-2h-furan-5-one Chemical compound O=C1OCC(CC=2C=CC=CC=2)=C1 NDSRBOXPULNFLZ-UHFFFAOYSA-N 0.000 claims 1
- 206010017788 Gastric haemorrhage Diseases 0.000 claims 1
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 238000004820 blood count Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical class O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 claims 1
- 206010043554 thrombocytopenia Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229960003957 dexamethasone Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 2
- 229960005285 mofebutazone Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- RLISWLLILOTWGG-UHFFFAOYSA-N salamidacetic acid Chemical compound NC(=O)C1=CC=CC=C1OCC(O)=O RLISWLLILOTWGG-UHFFFAOYSA-N 0.000 description 2
- 229950000417 salamidacetic acid Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- SEBVCBGKXLMBQW-UHFFFAOYSA-N 2-amino-2h-phenazin-1-one Chemical class C1=CC=C2N=C(C(C(N)C=C3)=O)C3=NC2=C1 SEBVCBGKXLMBQW-UHFFFAOYSA-N 0.000 description 1
- IQMGXSMKUXLLER-UHFFFAOYSA-N 2-hydroxy-5-sulfobenzoic acid;sodium Chemical compound [Na].OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O IQMGXSMKUXLLER-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WVKJXODDCGKPDX-UHFFFAOYSA-N mofebutazone sodium Chemical compound [Na+].O=C1[C-](CCCC)C(=O)NN1C1=CC=CC=C1 WVKJXODDCGKPDX-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 150000003218 pyrazolidines Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
Classifications
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT726571A AT320861B (de) | 1971-08-19 | 1971-08-19 | Verfahren zur Herstellung von wässerigen, hochkonzentrierten Lösungen von Dimethylaminophenazon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2236317A1 DE2236317A1 (de) | 1973-02-22 |
| DE2236317B2 true DE2236317B2 (de) | 1973-11-29 |
Family
ID=3594287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2236317A Pending DE2236317B2 (de) | 1971-08-19 | 1972-07-25 | Pharmazeutisches Präparat |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3865940A (Direct) |
| AT (1) | AT320861B (Direct) |
| BE (1) | BE787013A (Direct) |
| DD (1) | DD101816A5 (Direct) |
| DE (1) | DE2236317B2 (Direct) |
| ES (1) | ES405950A1 (Direct) |
| FR (1) | FR2150727B1 (Direct) |
| HU (1) | HU164074B (Direct) |
| LU (1) | LU65911A1 (Direct) |
| NL (1) | NL7211360A (Direct) |
| SU (1) | SU520877A3 (Direct) |
-
1971
- 1971-08-19 AT AT726571A patent/AT320861B/de not_active IP Right Cessation
-
1972
- 1972-07-25 DE DE2236317A patent/DE2236317B2/de active Pending
- 1972-07-31 BE BE787013A patent/BE787013A/xx unknown
- 1972-08-03 FR FR7228014A patent/FR2150727B1/fr not_active Expired
- 1972-08-10 US US279734A patent/US3865940A/en not_active Expired - Lifetime
- 1972-08-17 DD DD165113A patent/DD101816A5/xx unknown
- 1972-08-17 LU LU65911A patent/LU65911A1/xx unknown
- 1972-08-17 HU HUKI678A patent/HU164074B/hu unknown
- 1972-08-18 ES ES405950A patent/ES405950A1/es not_active Expired
- 1972-08-18 SU SU1820224A patent/SU520877A3/ru active
- 1972-08-18 NL NL7211360A patent/NL7211360A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU65911A1 (Direct) | 1973-01-15 |
| ES405950A1 (es) | 1975-08-01 |
| FR2150727B1 (Direct) | 1976-03-05 |
| SU520877A3 (ru) | 1976-07-05 |
| AT320861B (de) | 1975-03-10 |
| DD101816A5 (Direct) | 1973-11-20 |
| HU164074B (Direct) | 1973-12-28 |
| US3865940A (en) | 1975-02-11 |
| BE787013A (fr) | 1972-11-16 |
| DE2236317A1 (de) | 1973-02-22 |
| NL7211360A (Direct) | 1973-02-21 |
| FR2150727A1 (Direct) | 1973-04-13 |
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