NO132724B - - Google Patents
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- Publication number
- NO132724B NO132724B NO243371A NO243371A NO132724B NO 132724 B NO132724 B NO 132724B NO 243371 A NO243371 A NO 243371A NO 243371 A NO243371 A NO 243371A NO 132724 B NO132724 B NO 132724B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- preparation
- norbornyl
- cumene
- Prior art date
Links
- -1 4'-fluorobiphenylyl Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 6
- NZPZBZOBAKUNSK-UHFFFAOYSA-N (4-propan-2-ylphenyl)cyclooctane Chemical compound C1(CCCCCCC1)C1=CC=C(C=C1)C(C)C NZPZBZOBAKUNSK-UHFFFAOYSA-N 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- QHADCFKNCUQEMY-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)cyclooctene Chemical compound C1(=CC=C(C=C1)C1=CCCCCCC1)C(C)C QHADCFKNCUQEMY-UHFFFAOYSA-N 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- VHFUMYGQRORTLD-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)bicyclo[2.2.1]heptane Chemical compound C12C(CC(CC1)C2)C2=CC=C(C=C2)C(C)C VHFUMYGQRORTLD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LNIMROTXCVMMFO-UHFFFAOYSA-N 2-methoxy-1-phenoxy-4-propan-2-ylbenzene Chemical compound COC1=CC(C(C)C)=CC=C1OC1=CC=CC=C1 LNIMROTXCVMMFO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GPDATMGCLOLJBJ-UHFFFAOYSA-N 1-fluoro-4-(4-prop-1-en-2-ylphenyl)benzene Chemical compound CC(=C)C1=CC=C(C=C1)C1=CC=C(F)C=C1 GPDATMGCLOLJBJ-UHFFFAOYSA-N 0.000 description 1
- QEXXVUNNXGLCTB-UHFFFAOYSA-N 1-fluoro-4-(4-propan-2-ylphenyl)benzene Chemical compound C1=CC(C(C)C)=CC=C1C1=CC=C(F)C=C1 QEXXVUNNXGLCTB-UHFFFAOYSA-N 0.000 description 1
- PAMLTMDKARKMOU-UHFFFAOYSA-N 2-(3-methoxy-4-phenoxyphenyl)propan-2-ol Chemical compound COC=1C=C(C=CC1OC1=CC=CC=C1)C(C)(C)O PAMLTMDKARKMOU-UHFFFAOYSA-N 0.000 description 1
- SFJJGLUATPUIGV-UHFFFAOYSA-N 2-methoxy-1-phenoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=C(OC2=CC=CC=C2)C=CC(=C1)C(C)=C SFJJGLUATPUIGV-UHFFFAOYSA-N 0.000 description 1
- SOLBWDYJYPZLER-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)bicyclo[2.2.1]heptan-3-ol Chemical compound C1=CC(C(C)C)=CC=C1C1(O)C(C2)CCC2C1 SOLBWDYJYPZLER-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010037660 Pyrexia 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
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-BKFZFHPZSA-N platinum-200 Chemical compound [200Pt] BASFCYQUMIYNBI-BKFZFHPZSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO751753A NO751753L (pl) | 1970-11-20 | 1975-05-16 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9155970A | 1970-11-20 | 1970-11-20 | |
| US12923771A | 1971-03-29 | 1971-03-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132724B true NO132724B (pl) | 1975-09-15 |
| NO132724C NO132724C (pl) | 1975-12-22 |
Family
ID=26784083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO243371A NO132724C (pl) | 1970-11-20 | 1971-06-25 |
Country Status (6)
| Country | Link |
|---|---|
| AR (1) | AR205325A1 (pl) |
| AT (1) | ATA98074A (pl) |
| ES (3) | ES392719A1 (pl) |
| NO (1) | NO132724C (pl) |
| PL (1) | PL86932B1 (pl) |
| RO (2) | RO63814A (pl) |
-
1971
- 1971-06-25 AT AT9807471A patent/ATA98074A/de not_active IP Right Cessation
- 1971-06-25 NO NO243371A patent/NO132724C/no unknown
- 1971-06-28 PL PL17353571A patent/PL86932B1/pl unknown
- 1971-06-28 RO RO6748571A patent/RO63814A/ro unknown
- 1971-06-28 RO RO7184263A patent/RO68010A/ro unknown
- 1971-06-28 ES ES392719A patent/ES392719A1/es not_active Expired
-
1972
- 1972-01-01 AR AR24425972A patent/AR205325A1/es active
-
1974
- 1974-01-16 ES ES422352A patent/ES422352A1/es not_active Expired
- 1974-01-16 ES ES422351A patent/ES422351A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA98074A (de) | 1975-06-15 |
| ES392719A1 (es) | 1974-12-01 |
| RO68010A (ro) | 1980-12-30 |
| ES422351A1 (es) | 1976-07-16 |
| ES422352A1 (es) | 1976-10-01 |
| PL86932B1 (pl) | 1976-06-30 |
| RO63814A (fr) | 1979-01-15 |
| NO132724C (pl) | 1975-12-22 |
| AR205325A1 (es) | 1976-04-30 |
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