GB1561679A - 3,3 - diphenylpropylamine derivatives - Google Patents
3,3 - diphenylpropylamine derivatives Download PDFInfo
- Publication number
- GB1561679A GB1561679A GB22681/78A GB2268178A GB1561679A GB 1561679 A GB1561679 A GB 1561679A GB 22681/78 A GB22681/78 A GB 22681/78A GB 2268178 A GB2268178 A GB 2268178A GB 1561679 A GB1561679 A GB 1561679A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pharmaceutically acceptable
- acceptable salts
- mixture
- solution
- amine
- 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.)
- Expired
Links
- KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical class C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- -1 3 - phenylthiopropyl Chemical group 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 6
- KHLFAZWSFALWCN-UHFFFAOYSA-N 4-[3-(3,3-diphenylpropylamino)propylsulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SCCCNCCC(C=1C=CC=CC=1)C1=CC=CC=C1 KHLFAZWSFALWCN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000007972 injectable composition Substances 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- 239000000829 suppository Substances 0.000 claims description 4
- 239000012267 brine Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- QHSYTPWEKPPUCQ-UHFFFAOYSA-N n-methyl-3,3-diphenyl-n-(3-phenylsulfanylpropyl)propan-1-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(C)CCCSC1=CC=CC=C1 QHSYTPWEKPPUCQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 229960001701 chloroform Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000767 anti-ulcer Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- SLHSRCBFPHCSGL-UHFFFAOYSA-N (3-bromo-1-phenylpropyl)benzene Chemical compound C=1C=CC=CC=1C(CCBr)C1=CC=CC=C1 SLHSRCBFPHCSGL-UHFFFAOYSA-N 0.000 description 2
- NUWWGCMQIKROIJ-UHFFFAOYSA-N 3,3-diphenyl-n-(3-phenylsulfanylpropyl)propan-1-amine Chemical class C=1C=CC=CC=1SCCCNCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NUWWGCMQIKROIJ-UHFFFAOYSA-N 0.000 description 2
- BOXAQKOVJLKRPK-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-phenylpropan-1-amine Chemical compound C1=CC(OC)=CC=C1C(CCN)C1=CC=CC=C1 BOXAQKOVJLKRPK-UHFFFAOYSA-N 0.000 description 2
- QKGLUZCZUKTKCC-UHFFFAOYSA-N 3-bromopropylsulfanylbenzene Chemical compound BrCCCSC1=CC=CC=C1 QKGLUZCZUKTKCC-UHFFFAOYSA-N 0.000 description 2
- WXXPRERLDRLMTP-UHFFFAOYSA-N 4-[3-[3,3-diphenylpropyl(methyl)amino]propylsulfanyl]phenol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(C)CCCSC1=CC=C(O)C=C1 WXXPRERLDRLMTP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000001663 anti-spastic effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OSYDHFOHMZHXNJ-UHFFFAOYSA-N 1-(3-bromopropylsulfanyl)-4-methoxybenzene Chemical compound COC1=CC=C(SCCCBr)C=C1 OSYDHFOHMZHXNJ-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IHPRVZKJZGXTBQ-UHFFFAOYSA-N 3-chloropropan-1-amine;hydron;chloride Chemical compound Cl.NCCCCl IHPRVZKJZGXTBQ-UHFFFAOYSA-N 0.000 description 1
- XJESCJCYQFZYDZ-UHFFFAOYSA-N 3-phenylsulfanylpropan-1-amine Chemical compound NCCCSC1=CC=CC=C1 XJESCJCYQFZYDZ-UHFFFAOYSA-N 0.000 description 1
- YRJNRIPTEYAKDD-UHFFFAOYSA-N 4-(3-aminopropylsulfanyl)phenol Chemical compound NCCCSC1=CC=C(O)C=C1 YRJNRIPTEYAKDD-UHFFFAOYSA-N 0.000 description 1
- AQNOLWMUYSZMJS-UHFFFAOYSA-N 4-(3-aminopropylsulfanyl)phenol;hydrochloride Chemical compound Cl.NCCCSC1=CC=C(O)C=C1 AQNOLWMUYSZMJS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KEQUYPGOONHGBP-UHFFFAOYSA-N 4-[1-phenyl-3-(3-phenylsulfanylpropylamino)propyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)CCNCCCSC1=CC=CC=C1 KEQUYPGOONHGBP-UHFFFAOYSA-N 0.000 description 1
- ZBBHYEPYMNFZIJ-UHFFFAOYSA-N 4-[1-phenyl-3-(3-phenylsulfanylpropylamino)propyl]phenol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C(C=1C=CC=CC=1)CCNCCCSC1=CC=CC=C1 ZBBHYEPYMNFZIJ-UHFFFAOYSA-N 0.000 description 1
- NQUFHJRHEWGURP-UHFFFAOYSA-N 4-[3-[methyl(3-phenylsulfanylpropyl)amino]-1-phenylpropyl]phenol Chemical compound C=1C=CC=CC=1C(C=1C=CC(O)=CC=1)CCN(C)CCCSC1=CC=CC=C1 NQUFHJRHEWGURP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
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- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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- 102000004190 Enzymes Human genes 0.000 description 1
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- 150000000994 L-ascorbates Chemical class 0.000 description 1
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- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
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- 150000001299 aldehydes Chemical class 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- AIMQBJIJBOCYQA-UHFFFAOYSA-N n-methyl-3,3-diphenyl-n-(3-phenylsulfanylpropyl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(C)CCCSC1=CC=CC=C1 AIMQBJIJBOCYQA-UHFFFAOYSA-N 0.000 description 1
- AKEGHAUFMKCWGX-UHFFFAOYSA-N n-methyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)C1=CC=CC=C1 AKEGHAUFMKCWGX-UHFFFAOYSA-N 0.000 description 1
- ZRSBFNZFGANOFG-UHFFFAOYSA-N n-methyl-3,3-diphenylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)C1=CC=CC=C1 ZRSBFNZFGANOFG-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical class CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT03474/77A IT1080455B (it) | 1977-06-17 | 1977-06-17 | N 3 feniltiopropil 3.3 difenil propilammine sostituite dotate di attivita farmacologia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561679A true GB1561679A (en) | 1980-02-27 |
Family
ID=11108046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22681/78A Expired GB1561679A (en) | 1977-06-17 | 1978-05-25 | 3,3 - diphenylpropylamine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5430142A (de) |
| AT (1) | AT357141B (de) |
| BE (1) | BE867570A (de) |
| DE (1) | DE2825447A1 (de) |
| DK (1) | DK144064C (de) |
| ES (1) | ES470845A1 (de) |
| FR (1) | FR2394527A1 (de) |
| GB (1) | GB1561679A (de) |
| GR (1) | GR73140B (de) |
| IT (1) | IT1080455B (de) |
| NL (1) | NL7805617A (de) |
| NO (1) | NO145097C (de) |
| PT (1) | PT68122A (de) |
| SE (1) | SE7806945L (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991016302A1 (en) * | 1990-04-23 | 1991-10-31 | The Governors Of The University Of Alberta | Phenolic amine depigmenting and antimelanoma agents |
| US5395611A (en) * | 1990-04-24 | 1995-03-07 | The Governors Of The University Of Alberta | Phenolic amine depigmenting and antimelanoma agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO134800C (de) * | 1971-07-15 | 1976-12-15 | Alfa Farmaceutici Spa |
-
1977
- 1977-06-17 IT IT03474/77A patent/IT1080455B/it active
-
1978
- 1978-05-24 NL NL7805617A patent/NL7805617A/xx not_active Application Discontinuation
- 1978-05-25 GB GB22681/78A patent/GB1561679A/en not_active Expired
- 1978-05-29 BE BE2057020A patent/BE867570A/xx unknown
- 1978-05-31 PT PT68122A patent/PT68122A/pt unknown
- 1978-06-09 DE DE19782825447 patent/DE2825447A1/de not_active Withdrawn
- 1978-06-13 AT AT430078A patent/AT357141B/de not_active IP Right Cessation
- 1978-06-13 FR FR7817593A patent/FR2394527A1/fr active Granted
- 1978-06-15 DK DK269278A patent/DK144064C/da active
- 1978-06-16 NO NO782101A patent/NO145097C/no unknown
- 1978-06-16 GR GR56534A patent/GR73140B/el unknown
- 1978-06-16 ES ES470845A patent/ES470845A1/es not_active Expired
- 1978-06-16 JP JP7310378A patent/JPS5430142A/ja active Pending
- 1978-06-16 SE SE7806945A patent/SE7806945L/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991016302A1 (en) * | 1990-04-23 | 1991-10-31 | The Governors Of The University Of Alberta | Phenolic amine depigmenting and antimelanoma agents |
| US5395611A (en) * | 1990-04-24 | 1995-03-07 | The Governors Of The University Of Alberta | Phenolic amine depigmenting and antimelanoma agents |
Also Published As
| Publication number | Publication date |
|---|---|
| NO782101L (no) | 1978-12-19 |
| BE867570A (fr) | 1978-09-18 |
| NO145097B (no) | 1981-10-05 |
| IT1080455B (it) | 1985-05-16 |
| NO145097C (no) | 1982-01-13 |
| DE2825447A1 (de) | 1979-01-04 |
| PT68122A (en) | 1978-06-01 |
| GR73140B (de) | 1984-02-08 |
| FR2394527B1 (de) | 1980-06-20 |
| ATA430078A (de) | 1979-11-15 |
| AT357141B (de) | 1980-06-25 |
| DK269278A (da) | 1978-12-18 |
| DK144064B (da) | 1981-11-30 |
| FR2394527A1 (fr) | 1979-01-12 |
| SE7806945L (sv) | 1978-12-18 |
| DK144064C (da) | 1982-06-21 |
| ES470845A1 (es) | 1979-09-01 |
| NL7805617A (nl) | 1978-12-19 |
| JPS5430142A (en) | 1979-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |