DE1618632B1 - Verfahren zur Herstellung von trans-4-Phenylcyclohexylamin-Salzen von Alfa-(4-Bipheny)-alkansäuren und entzündungshemmenden und Schmerzlindernden Eigenschaften - Google Patents
Verfahren zur Herstellung von trans-4-Phenylcyclohexylamin-Salzen von Alfa-(4-Bipheny)-alkansäuren und entzündungshemmenden und Schmerzlindernden EigenschaftenInfo
- Publication number
- DE1618632B1 DE1618632B1 DE1967M0072375 DEM0072375A DE1618632B1 DE 1618632 B1 DE1618632 B1 DE 1618632B1 DE 1967M0072375 DE1967M0072375 DE 1967M0072375 DE M0072375 A DEM0072375 A DE M0072375A DE 1618632 B1 DE1618632 B1 DE 1618632B1
- Authority
- DE
- Germany
- Prior art keywords
- trans
- phenylcyclohexylamine
- salts
- inflammatory
- preparation
- 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
- 239000002253 acid Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- SJISCEAZUHNOMD-HAQNSBGRSA-N C1C[C@@H](N)CC[C@@H]1C1=CC=CC=C1 Chemical class C1C[C@@H](N)CC[C@@H]1C1=CC=CC=C1 SJISCEAZUHNOMD-HAQNSBGRSA-N 0.000 title claims description 4
- 150000007513 acids Chemical class 0.000 title claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 208000002193 Pain Diseases 0.000 title description 4
- 230000036407 pain Effects 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 8
- -1 4-biphenylyl Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000001760 anti-analgesic effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- SJISCEAZUHNOMD-UHFFFAOYSA-N 4-phenylcyclohexan-1-amine Chemical compound C1CC(N)CCC1C1=CC=CC=C1 SJISCEAZUHNOMD-UHFFFAOYSA-N 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 208000000114 Pain Threshold Diseases 0.000 description 5
- 230000037040 pain threshold Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229960000212 aminophenazone Drugs 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 2
- JTLAHVRPWDIEMU-UHFFFAOYSA-N n-(4-phenylcyclohexylidene)hydroxylamine Chemical compound C1CC(=NO)CCC1C1=CC=CC=C1 JTLAHVRPWDIEMU-UHFFFAOYSA-N 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- 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 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MDLKWDQMIZRIBY-UHFFFAOYSA-N 1-(dimethylamino)ethanol Chemical class CC(O)N(C)C MDLKWDQMIZRIBY-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 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
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- WCNLCIJMFAJCPX-UHFFFAOYSA-N pethidine hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 WCNLCIJMFAJCPX-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- IYEPZNKOJZOGJG-UHFFFAOYSA-N xenbucin Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1C1=CC=CC=C1 IYEPZNKOJZOGJG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1339866 | 1966-01-14 | ||
| IT1952966 | 1966-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618632B1 true DE1618632B1 (de) | 1971-11-11 |
Family
ID=26326642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967M0072375 Pending DE1618632B1 (de) | 1966-01-14 | 1967-01-11 | Verfahren zur Herstellung von trans-4-Phenylcyclohexylamin-Salzen von Alfa-(4-Bipheny)-alkansäuren und entzündungshemmenden und Schmerzlindernden Eigenschaften |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE692583A (enrdf_load_stackoverflow) |
| DE (1) | DE1618632B1 (enrdf_load_stackoverflow) |
| DK (1) | DK126107B (enrdf_load_stackoverflow) |
| ES (1) | ES335177A1 (enrdf_load_stackoverflow) |
| GR (1) | GR33295B (enrdf_load_stackoverflow) |
| NO (1) | NO123427B (enrdf_load_stackoverflow) |
| SE (1) | SE324764B (enrdf_load_stackoverflow) |
-
1966
- 1966-12-30 DK DK677866A patent/DK126107B/da unknown
-
1967
- 1967-01-02 ES ES0335177A patent/ES335177A1/es not_active Expired
- 1967-01-09 NO NO16631467A patent/NO123427B/no unknown
- 1967-01-10 GR GR670133295A patent/GR33295B/el unknown
- 1967-01-11 SE SE40867A patent/SE324764B/xx unknown
- 1967-01-11 DE DE1967M0072375 patent/DE1618632B1/de active Pending
- 1967-01-13 BE BE692583D patent/BE692583A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| NO123427B (enrdf_load_stackoverflow) | 1971-11-15 |
| SE324764B (enrdf_load_stackoverflow) | 1970-06-15 |
| GR33295B (el) | 1967-11-21 |
| DK126107B (da) | 1973-06-12 |
| BE692583A (enrdf_load_stackoverflow) | 1967-06-16 |
| ES335177A1 (es) | 1967-11-16 |
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