NO842885L - Fremgangsmaate ved fremstilling av terapeutisk akive 9-anthryuloxyaminoalkaner og beslektede forbindelser - Google Patents
Fremgangsmaate ved fremstilling av terapeutisk akive 9-anthryuloxyaminoalkaner og beslektede forbindelserInfo
- Publication number
- NO842885L NO842885L NO842885A NO842885A NO842885L NO 842885 L NO842885 L NO 842885L NO 842885 A NO842885 A NO 842885A NO 842885 A NO842885 A NO 842885A NO 842885 L NO842885 L NO 842885L
- Authority
- NO
- Norway
- Prior art keywords
- anthryloxy
- formula
- compound
- pharmaceutically acceptable
- acid addition
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 126
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title description 25
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 44
- -1 cyano, carbamoyl Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical group 0.000 claims description 7
- AAIGTATUYZIFRC-UHFFFAOYSA-N 4-anthracen-9-yloxybutan-1-amine Chemical compound C1=CC=C2C(OCCCCN)=C(C=CC=C3)C3=CC2=C1 AAIGTATUYZIFRC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- DTDHSBBEVQVBTK-UHFFFAOYSA-N 2-anthracen-9-yloxyethanamine Chemical compound C1=CC=C2C(OCCN)=C(C=CC=C3)C3=CC2=C1 DTDHSBBEVQVBTK-UHFFFAOYSA-N 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- HDGKBUNYCAFLBC-UHFFFAOYSA-N 2-anthracen-9-yloxy-n,n-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=C(C=CC=C3)C3=CC2=C1 HDGKBUNYCAFLBC-UHFFFAOYSA-N 0.000 claims description 3
- SDDAGHHAJBIUDD-UHFFFAOYSA-N 3-anthracen-9-yloxy-n,n-dimethylpropan-1-amine Chemical compound C1=CC=C2C(OCCCN(C)C)=C(C=CC=C3)C3=CC2=C1 SDDAGHHAJBIUDD-UHFFFAOYSA-N 0.000 claims description 3
- BXNAAWUCZVLZKQ-UHFFFAOYSA-N 3-anthracen-9-yloxypropan-1-amine Chemical compound C1=CC=C2C(OCCCN)=C(C=CC=C3)C3=CC2=C1 BXNAAWUCZVLZKQ-UHFFFAOYSA-N 0.000 claims description 3
- GAVLGJFQZUKFEQ-UHFFFAOYSA-N 4-anthracen-9-yloxy-n,n-dimethylbutan-1-amine Chemical compound C1=CC=C2C(OCCCCN(C)C)=C(C=CC=C3)C3=CC2=C1 GAVLGJFQZUKFEQ-UHFFFAOYSA-N 0.000 claims description 3
- XHWYYORGXDZUOS-UHFFFAOYSA-N 5-anthracen-9-yloxypentan-1-amine Chemical compound C1=CC=C2C(OCCCCCN)=C(C=CC=C3)C3=CC2=C1 XHWYYORGXDZUOS-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- 241000124008 Mammalia Species 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- XLXDPEINDSPEHY-UHFFFAOYSA-N 6-anthracen-9-yloxyhexan-1-amine Chemical compound C1=CC=C2C(OCCCCCCN)=C(C=CC=C3)C3=CC2=C1 XLXDPEINDSPEHY-UHFFFAOYSA-N 0.000 claims description 2
- HUQIXLHGWPTZMU-UHFFFAOYSA-N 8-anthracen-9-yloxy-n,n-dimethyloctan-1-amine Chemical compound C1=CC=C2C(OCCCCCCCCN(C)C)=C(C=CC=C3)C3=CC2=C1 HUQIXLHGWPTZMU-UHFFFAOYSA-N 0.000 claims description 2
- MNZJGPHEBLWDLV-UHFFFAOYSA-N 8-anthracen-9-yloxyoctan-1-amine Chemical compound C1=CC=C2C(OCCCCCCCCN)=C(C=CC=C3)C3=CC2=C1 MNZJGPHEBLWDLV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
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- 150000008425 anthrones Chemical class 0.000 description 15
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- 238000010992 reflux Methods 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
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- 230000009467 reduction Effects 0.000 description 13
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000002552 dosage form Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
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- 239000010452 phosphate Substances 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 7
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
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- 230000003110 anti-inflammatory effect Effects 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
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- AGNRKKIEIMSSHW-UHFFFAOYSA-N 2-(2-anthracen-9-yloxyethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCOC1=C(C=CC=C2)C2=CC2=CC=CC=C12 AGNRKKIEIMSSHW-UHFFFAOYSA-N 0.000 description 4
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- WTWGPZKBZSXPCI-UHFFFAOYSA-N 9-(4-chlorobutoxy)anthracene Chemical compound C1=CC=C2C(OCCCCCl)=C(C=CC=C3)C3=CC2=C1 WTWGPZKBZSXPCI-UHFFFAOYSA-N 0.000 description 1
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- UKNLNELVKVBRLC-UHFFFAOYSA-N 9-(6-chlorohexoxy)anthracene Chemical compound C1=CC=C2C(OCCCCCCCl)=C(C=CC=C3)C3=CC2=C1 UKNLNELVKVBRLC-UHFFFAOYSA-N 0.000 description 1
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- OCSQZBSBUUSDCW-UHFFFAOYSA-N 9-(9-chlorononoxy)-2-methoxyanthracene Chemical compound C1=CC=CC2=C(OCCCCCCCCCCl)C3=CC(OC)=CC=C3C=C21 OCSQZBSBUUSDCW-UHFFFAOYSA-N 0.000 description 1
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
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- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
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- 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- UJTYCTADLATUKX-UHFFFAOYSA-N n,n-dimethyl-12-(1-methylanthracen-9-yl)oxydodecan-1-amine Chemical compound C1=CC(C)=C2C(OCCCCCCCCCCCCN(C)C)=C(C=CC=C3)C3=CC2=C1 UJTYCTADLATUKX-UHFFFAOYSA-N 0.000 description 1
- MYVYCNWLXNYRKO-UHFFFAOYSA-N n,n-dimethyl-3-(2-methylanthracen-9-yl)oxypropan-1-amine Chemical compound C1=C(C)C=C2C(OCCCN(C)C)=C(C=CC=C3)C3=CC2=C1 MYVYCNWLXNYRKO-UHFFFAOYSA-N 0.000 description 1
- NJRLGQXKFMMMNY-UHFFFAOYSA-N n,n-dimethyl-4-(4-methylanthracen-9-yl)oxybutan-1-amine Chemical compound C1=CC=C2C(OCCCCN(C)C)=C(C=CC=C3)C3=CC2=C1C NJRLGQXKFMMMNY-UHFFFAOYSA-N 0.000 description 1
- VIDLLRHYOFQPJF-UHFFFAOYSA-N n,n-dimethyl-6-(1,4,5,7-tetramethylanthracen-9-yl)oxyhexan-1-amine Chemical compound C1=CC(C)=C2C(OCCCCCCN(C)C)=C(C=C(C)C=C3C)C3=CC2=C1C VIDLLRHYOFQPJF-UHFFFAOYSA-N 0.000 description 1
- WHCZCLAPYHXBLX-UHFFFAOYSA-N n,n-dimethyl-7-(1,4,6-trimethoxyanthracen-9-yl)oxyheptan-1-amine Chemical compound COC1=CC=C(OC)C2=CC3=CC(OC)=CC=C3C(OCCCCCCCN(C)C)=C21 WHCZCLAPYHXBLX-UHFFFAOYSA-N 0.000 description 1
- GOXPMVHQGRUACC-UHFFFAOYSA-N n-ethyl-4-(4-methylanthracen-9-yl)oxybutan-1-amine Chemical compound C1=CC=C2C(OCCCCNCC)=C(C=CC=C3)C3=CC2=C1C GOXPMVHQGRUACC-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000006174 pH buffer Substances 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
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- 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 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- 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)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/514,112 US4792551A (en) | 1983-07-15 | 1983-07-15 | 9-anthryloxyaminoalkanes and related compounds as anti-inflammatory and analgetic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO842885L true NO842885L (no) | 1985-01-16 |
Family
ID=24045842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO842885A NO842885L (no) | 1983-07-15 | 1984-07-13 | Fremgangsmaate ved fremstilling av terapeutisk akive 9-anthryuloxyaminoalkaner og beslektede forbindelser |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4792551A (es) |
| EP (1) | EP0132351A3 (es) |
| JP (1) | JPS6038348A (es) |
| KR (1) | KR850001186A (es) |
| AU (1) | AU3059484A (es) |
| CS (1) | CS244140B2 (es) |
| DK (1) | DK347084A (es) |
| ES (2) | ES8606838A1 (es) |
| FI (1) | FI842835A (es) |
| GR (1) | GR81443B (es) |
| HU (1) | HUT34433A (es) |
| IL (1) | IL72408A0 (es) |
| NO (1) | NO842885L (es) |
| PL (3) | PL254103A1 (es) |
| PT (1) | PT78906A (es) |
| ZA (1) | ZA845444B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5354689A (en) * | 1993-05-10 | 1994-10-11 | The United States Of America As Represented By The Department Of Health And Human Services | Method of detecting isocyanates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL237664A (es) * | 1959-04-01 | |||
| US3304307A (en) * | 1963-09-12 | 1967-02-14 | Ciba Geigy Corp | Dibenzocycloalkadienes |
| FR176F (es) * | 1965-05-19 | |||
| US3579582A (en) * | 1967-02-16 | 1971-05-18 | Universal Oil Prod Co | Hydroxy and/or hydrocarbyloxy and amino substituted tetrahydronaphthalenes |
| US3493616A (en) * | 1967-02-27 | 1970-02-03 | Universal Oil Prod Co | Hydroxy and/or hydrocarbyloxy and amino-alkano-tetrahydronaphthalenes |
| CH558774A (de) * | 1971-02-23 | 1975-02-14 | Ciba Geigy Ag | Verfahren zur herstellung neuer 9-(2-hydroxy-3-aminopropyl-9,10-dihydro-9,10-aethanoanthracene. |
| US3816430A (en) * | 1972-10-30 | 1974-06-11 | American Home Prod | N,n'-(naphthylenedioxydiethylene)bis(di(lower)alkylamines)and the salts thereof |
| US4127717A (en) * | 1978-03-20 | 1978-11-28 | E. R. Squibb & Sons, Inc. | Benzo-cyclitolamines |
-
1983
- 1983-07-15 US US06/514,112 patent/US4792551A/en not_active Expired - Fee Related
-
1984
- 1984-07-13 PL PL25410384A patent/PL254103A1/xx unknown
- 1984-07-13 FI FI842835A patent/FI842835A/fi not_active Application Discontinuation
- 1984-07-13 DK DK347084A patent/DK347084A/da not_active Application Discontinuation
- 1984-07-13 PL PL25410284A patent/PL254102A1/xx unknown
- 1984-07-13 NO NO842885A patent/NO842885L/no unknown
- 1984-07-13 EP EP84304792A patent/EP0132351A3/en not_active Withdrawn
- 1984-07-13 ZA ZA845444A patent/ZA845444B/xx unknown
- 1984-07-13 GR GR75293A patent/GR81443B/el unknown
- 1984-07-13 KR KR1019840004131A patent/KR850001186A/ko not_active Application Discontinuation
- 1984-07-13 PT PT78906A patent/PT78906A/pt unknown
- 1984-07-13 AU AU30594/84A patent/AU3059484A/en not_active Abandoned
- 1984-07-13 PL PL24873084A patent/PL248730A1/xx unknown
- 1984-07-13 HU HU842739A patent/HUT34433A/hu unknown
- 1984-07-13 CS CS845462A patent/CS244140B2/cs unknown
- 1984-07-13 IL IL72408A patent/IL72408A0/xx unknown
- 1984-07-13 JP JP59146684A patent/JPS6038348A/ja active Pending
-
1985
- 1985-07-16 ES ES545266A patent/ES8606838A1/es not_active Expired
- 1985-07-16 ES ES545265A patent/ES8603164A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL72408A0 (en) | 1984-11-30 |
| PL254103A1 (en) | 1986-05-20 |
| ES545265A0 (es) | 1986-01-01 |
| ES8603164A1 (es) | 1986-01-01 |
| ES545266A0 (es) | 1986-05-16 |
| PL254102A1 (en) | 1986-05-20 |
| EP0132351A2 (en) | 1985-01-30 |
| HUT34433A (en) | 1985-03-28 |
| GR81443B (es) | 1984-12-11 |
| PL248730A1 (en) | 1985-12-17 |
| AU3059484A (en) | 1985-01-17 |
| PT78906A (en) | 1984-08-01 |
| DK347084A (da) | 1985-01-16 |
| EP0132351A3 (en) | 1985-10-30 |
| ES8606838A1 (es) | 1986-05-16 |
| KR850001186A (ko) | 1985-03-16 |
| JPS6038348A (ja) | 1985-02-27 |
| ZA845444B (en) | 1987-02-25 |
| FI842835A (fi) | 1985-01-16 |
| US4792551A (en) | 1988-12-20 |
| CS546284A2 (en) | 1985-08-15 |
| CS244140B2 (en) | 1986-07-17 |
| DK347084D0 (da) | 1984-07-13 |
| FI842835A0 (fi) | 1984-07-13 |
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