DE1693031B1 - Dipropylacetanilid- und dipropylacetylsalicylsaeurederivate, ihre herstellung und diese enthaltende pharmazeutische mittel - Google Patents
Dipropylacetanilid- und dipropylacetylsalicylsaeurederivate, ihre herstellung und diese enthaltende pharmazeutische mittelInfo
- Publication number
- DE1693031B1 DE1693031B1 DE19671693031 DE1693031A DE1693031B1 DE 1693031 B1 DE1693031 B1 DE 1693031B1 DE 19671693031 DE19671693031 DE 19671693031 DE 1693031 A DE1693031 A DE 1693031A DE 1693031 B1 DE1693031 B1 DE 1693031B1
- Authority
- DE
- Germany
- Prior art keywords
- animals
- dipropyl
- acetanilide
- product
- test
- 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
- ROHAROKRAREQAZ-UHFFFAOYSA-N n-phenyl-2-propylpentanamide Chemical compound CCCC(CCC)C(=O)NC1=CC=CC=C1 ROHAROKRAREQAZ-UHFFFAOYSA-N 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 title description 2
- -1 DIPROPYL ACETYL SALICYL Chemical class 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 229940127557 pharmaceutical product Drugs 0.000 title 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 16
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 6
- 229960001413 acetanilide Drugs 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 description 51
- 239000000047 product Substances 0.000 description 41
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
- 238000012360 testing method Methods 0.000 description 19
- 229960001138 acetylsalicylic acid Drugs 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- 208000002193 Pain Diseases 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000005995 Aluminium silicate Substances 0.000 description 11
- 235000012211 aluminium silicate Nutrition 0.000 description 11
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 230000000202 analgesic effect Effects 0.000 description 8
- 235000019256 formaldehyde Nutrition 0.000 description 8
- 229960004279 formaldehyde Drugs 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- PITHYUDHKJKJNQ-UHFFFAOYSA-N 2-propylpentanoyl chloride Chemical compound CCCC(C(Cl)=O)CCC PITHYUDHKJKJNQ-UHFFFAOYSA-N 0.000 description 5
- 206010019233 Headaches Diseases 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 210000000548 hind-foot Anatomy 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- HILHGPGUHSJXAX-UHFFFAOYSA-N 2-(2-propylpentanoyloxy)benzoic acid Chemical compound CCCC(CCC)C(=O)OC1=CC=CC=C1C(O)=O HILHGPGUHSJXAX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 210000000629 knee joint Anatomy 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- 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 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 206010020843 Hyperthermia Diseases 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- 239000002221 antipyretic Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000036031 hyperthermia Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SRXFVOCKFFIODY-UHFFFAOYSA-N FC(C(C(=O)NC1=CC=CC=C1)(CCC)CCC)(F)F Chemical compound FC(C(C(=O)NC1=CC=CC=C1)(CCC)CCC)(F)F SRXFVOCKFFIODY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 210000001061 forehead Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- JRLJKNVORZMXAF-UHFFFAOYSA-N n-(4-hydroxyphenyl)-2-propylpentanamide Chemical compound CCCC(CCC)C(=O)NC1=CC=C(O)C=C1 JRLJKNVORZMXAF-UHFFFAOYSA-N 0.000 description 2
- 229940124641 pain reliever Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FTRNUAWSYMYHAH-UHFFFAOYSA-N (2-carbamoylphenyl) 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OC1=CC=CC=C1C(N)=O FTRNUAWSYMYHAH-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 1
- AJRRTLFGKAVXCQ-UHFFFAOYSA-N 2-hydroxy-3,4-dipropylbenzamide Chemical compound C(CC)C=1C(=C(C(C(=O)N)=CC1)O)CCC AJRRTLFGKAVXCQ-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 241001237754 Algia Species 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010020462 Humerus fracture Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000036071 Rhinorrhea Diseases 0.000 description 1
- 206010039101 Rhinorrhoea Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000018984 mastication Effects 0.000 description 1
- 238000010077 mastication Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 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
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A23B2/762—Organic compounds containing nitrogen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR81021A FR6999M (enrdf_load_stackoverflow) | 1966-10-21 | 1966-10-21 | |
| FR91010A FR1507886A (fr) | 1967-01-13 | 1967-01-13 | Nouveaux dérivés du dipropylacétylanilide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1693031B1 true DE1693031B1 (de) | 1973-02-15 |
| DE1693031C2 DE1693031C2 (enrdf_load_stackoverflow) | 1973-10-31 |
Family
ID=26173833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671693031 Granted DE1693031B1 (de) | 1966-10-21 | 1967-10-20 | Dipropylacetanilid- und dipropylacetylsalicylsaeurederivate, ihre herstellung und diese enthaltende pharmazeutische mittel |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1693031B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1201190A (enrdf_load_stackoverflow) |
-
1967
- 1967-10-12 GB GB46670/67A patent/GB1201190A/en not_active Expired
- 1967-10-20 DE DE19671693031 patent/DE1693031B1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1693031C2 (enrdf_load_stackoverflow) | 1973-10-31 |
| GB1201190A (en) | 1970-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |