CA1116636A - Alkylthiophenoxypropanolamines - Google Patents
AlkylthiophenoxypropanolaminesInfo
- Publication number
- CA1116636A CA1116636A CA000312115A CA312115A CA1116636A CA 1116636 A CA1116636 A CA 1116636A CA 000312115 A CA000312115 A CA 000312115A CA 312115 A CA312115 A CA 312115A CA 1116636 A CA1116636 A CA 1116636A
- Authority
- CA
- Canada
- Prior art keywords
- phenoxy
- propanol
- methylethyl
- thio
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 58
- ZAPDURRCHSKKKK-UHFFFAOYSA-N 1-(octylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol Chemical compound CCCCCCCCNCC(O)COC1=CC=C(SC(C)C)C=C1 ZAPDURRCHSKKKK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 230000008569 process Effects 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- -1 primary amino compound Chemical class 0.000 claims description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 24
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 12
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 8
- DVDGHEZGPNPQAV-UHFFFAOYSA-N 4-propan-2-ylsulfanylphenol Chemical compound CC(C)SC1=CC=C(O)C=C1 DVDGHEZGPNPQAV-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- NJIYJKALGDCITC-UHFFFAOYSA-N 1-(2-methyl-4-methylsulfanylphenoxy)-3-(octylamino)propan-2-ol Chemical compound CCCCCCCCNCC(O)COC1=CC=C(SC)C=C1C NJIYJKALGDCITC-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- GCYUSDHZIAFXPD-UHFFFAOYSA-N 1-(2-methylsulfanylphenoxy)-3-(octylamino)propan-2-ol Chemical compound CCCCCCCCNCC(O)COC1=CC=CC=C1SC GCYUSDHZIAFXPD-UHFFFAOYSA-N 0.000 claims description 4
- ZGRXEJDDZVCITI-UHFFFAOYSA-N 1-(dodecylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol Chemical compound CCCCCCCCCCCCNCC(O)COC1=CC=C(SC(C)C)C=C1 ZGRXEJDDZVCITI-UHFFFAOYSA-N 0.000 claims description 4
- VORNLKLJEMSFFV-UHFFFAOYSA-N 1-(2-cyclohexylethylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol Chemical compound C1=CC(SC(C)C)=CC=C1OCC(O)CNCCC1CCCCC1 VORNLKLJEMSFFV-UHFFFAOYSA-N 0.000 claims description 3
- IAGFVCWQMCZABO-UHFFFAOYSA-N 1-(4-methylsulfanylphenoxy)-3-(octylamino)propan-2-ol Chemical compound CCCCCCCCNCC(O)COC1=CC=C(SC)C=C1 IAGFVCWQMCZABO-UHFFFAOYSA-N 0.000 claims description 3
- SENNKTSISNNSHS-UHFFFAOYSA-N 1-(octylamino)-3-(3-propan-2-ylsulfanylphenoxy)propan-2-ol Chemical compound CCCCCCCCNCC(O)COC1=CC=CC(SC(C)C)=C1 SENNKTSISNNSHS-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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- RZLLASOLDHULHD-UHFFFAOYSA-N 1-(2-methylsulfanylphenoxy)-3-(octylamino)propan-2-ol;hydrochloride Chemical compound Cl.CCCCCCCCNCC(O)COC1=CC=CC=C1SC RZLLASOLDHULHD-UHFFFAOYSA-N 0.000 claims description 2
- MDYVTFJMMYVONT-UHFFFAOYSA-N 1-(4-cyclohexylbutylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol;hydrochloride Chemical compound Cl.C1=CC(SC(C)C)=CC=C1OCC(O)CNCCCCC1CCCCC1 MDYVTFJMMYVONT-UHFFFAOYSA-N 0.000 claims description 2
- DXLSPFDSUIZAON-UHFFFAOYSA-N 2-methyl-4-methylsulfanylphenol Chemical compound CSC1=CC=C(O)C(C)=C1 DXLSPFDSUIZAON-UHFFFAOYSA-N 0.000 claims description 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 claims description 2
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 claims 2
- WNUPSSMAWGRQOS-UHFFFAOYSA-N 1-(2-cyclohexylethylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol;hydrochloride Chemical compound Cl.C1=CC(SC(C)C)=CC=C1OCC(O)CNCCC1CCCCC1 WNUPSSMAWGRQOS-UHFFFAOYSA-N 0.000 claims 1
- XWGFCGCMXBSIRJ-UHFFFAOYSA-N 1-(4-cyclohexylbutylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol Chemical compound C1=CC(SC(C)C)=CC=C1OCC(O)CNCCCCC1CCCCC1 XWGFCGCMXBSIRJ-UHFFFAOYSA-N 0.000 claims 1
- VTUJBLPPNLCDFB-UHFFFAOYSA-N 1-(octylamino)-3-(3-propan-2-ylsulfanylphenoxy)propan-2-ol;hydrochloride Chemical compound Cl.CCCCCCCCNCC(O)COC1=CC=CC(SC(C)C)=C1 VTUJBLPPNLCDFB-UHFFFAOYSA-N 0.000 claims 1
- QFKMDZYQWDSMPA-UHFFFAOYSA-N 1-(octylamino)-3-(4-propan-2-ylsulfanylphenoxy)propan-2-ol;hydrochloride Chemical compound Cl.CCCCCCCCNCC(O)COC1=CC=C(SC(C)C)C=C1 QFKMDZYQWDSMPA-UHFFFAOYSA-N 0.000 claims 1
- AUHGURNMOWDGBF-UHFFFAOYSA-N 3-propan-2-ylsulfanylphenol Chemical compound CC(C)SC1=CC=CC(O)=C1 AUHGURNMOWDGBF-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 12
- 230000002921 anti-spasmodic effect Effects 0.000 abstract description 11
- 230000000304 vasodilatating effect Effects 0.000 abstract description 10
- 210000001772 blood platelet Anatomy 0.000 abstract description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 6
- 230000002490 cerebral effect Effects 0.000 abstract description 2
- 230000000414 obstructive effect Effects 0.000 abstract description 2
- 230000002792 vascular Effects 0.000 abstract description 2
- 230000024883 vasodilation Effects 0.000 abstract description 2
- 208000018262 Peripheral vascular disease Diseases 0.000 abstract 1
- 230000007812 deficiency Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 50
- 239000000243 solution Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000003795 chemical substances by application Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 20
- 238000007792 addition Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 210000001519 tissue Anatomy 0.000 description 13
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 12
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 230000004044 response Effects 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 241000283973 Oryctolagus cuniculus Species 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 7
- 239000000812 cholinergic antagonist Substances 0.000 description 7
- 230000036515 potency Effects 0.000 description 7
- 229940124549 vasodilator Drugs 0.000 description 7
- 239000003071 vasodilator agent Substances 0.000 description 7
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- 229960001789 papaverine Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 238000001802 infusion Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229940039009 isoproterenol Drugs 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- SUMWYVVUFJCTQX-UHFFFAOYSA-N 2,2-dimethylhexan-1-amine Chemical compound CCCCC(C)(C)CN SUMWYVVUFJCTQX-UHFFFAOYSA-N 0.000 description 4
- GFKABXPATHSPAB-UHFFFAOYSA-N 2-(4-propan-2-ylsulfanylphenoxy)acetaldehyde Chemical compound CC(C)SC1=CC=C(OCC=O)C=C1 GFKABXPATHSPAB-UHFFFAOYSA-N 0.000 description 4
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 210000000709 aorta Anatomy 0.000 description 4
- 210000002376 aorta thoracic Anatomy 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
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- 238000007796 conventional method Methods 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- OHMXXZIUOWNPRG-UHFFFAOYSA-N 2-methyloctan-2-amine Chemical compound CCCCCCC(C)(C)N OHMXXZIUOWNPRG-UHFFFAOYSA-N 0.000 description 3
- MXFVXKGNZWGEJK-UHFFFAOYSA-N 3-amino-3-methyl-1-(4-propan-2-ylsulfanylphenoxy)butan-2-ol Chemical compound CC(C)SC1=CC=C(OCC(O)C(C)(C)N)C=C1 MXFVXKGNZWGEJK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000007101 Muscle Cramp Diseases 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
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- 238000000338 in vitro Methods 0.000 description 3
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- 230000003993 interaction Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 210000003141 lower extremity Anatomy 0.000 description 3
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- 230000010412 perfusion Effects 0.000 description 3
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- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 3
- 229960001999 phentolamine Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 230000002885 thrombogenetic effect Effects 0.000 description 3
- 208000019553 vascular disease Diseases 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LXVMQKREAPQFPN-UHFFFAOYSA-N 2,2-dimethylhexanenitrile Chemical compound CCCCC(C)(C)C#N LXVMQKREAPQFPN-UHFFFAOYSA-N 0.000 description 2
- ABROBCBIIWHVNS-UHFFFAOYSA-N 2-Ethylbenzenethiol Chemical compound CCC1=CC=CC=C1S ABROBCBIIWHVNS-UHFFFAOYSA-N 0.000 description 2
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- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 description 1
- MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229960003054 gallamine Drugs 0.000 description 1
- ICLWTJIMXVISSR-UHFFFAOYSA-N gallamine Chemical compound CCN(CC)CCOC1=CC=CC(OCCN(CC)CC)=C1OCCN(CC)CC ICLWTJIMXVISSR-UHFFFAOYSA-N 0.000 description 1
- 229960005271 gallamine triethiodide Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VRYPROVLGPMATH-UHFFFAOYSA-N n-benzyloctan-1-amine Chemical compound CCCCCCCCNCC1=CC=CC=C1 VRYPROVLGPMATH-UHFFFAOYSA-N 0.000 description 1
- PEIJPMBOGRPKQJ-UHFFFAOYSA-N n-benzylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCC1=CC=CC=C1 PEIJPMBOGRPKQJ-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940061319 ovide Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 208000028591 pheochromocytoma Diseases 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 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
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- CSUNLSYSEQIDMO-UHFFFAOYSA-N tiprenolol Chemical compound CSC1=CC=CC=C1OCC(O)CNC(C)C CSUNLSYSEQIDMO-UHFFFAOYSA-N 0.000 description 1
- 229950004988 tiprenolol Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000005090 tracheal smooth muscle Anatomy 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 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
- C07C323/31—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 atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—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 atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84116877A | 1977-10-11 | 1977-10-11 | |
| US841,168 | 1977-10-11 | ||
| US94222278A | 1978-09-14 | 1978-09-14 | |
| US942,222 | 1978-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1116636A true CA1116636A (en) | 1982-01-19 |
Family
ID=27126241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000312115A Expired CA1116636A (en) | 1977-10-11 | 1978-09-26 | Alkylthiophenoxypropanolamines |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS6049188B2 (de) |
| AR (2) | AR224239A1 (de) |
| AU (1) | AU520181B2 (de) |
| CA (1) | CA1116636A (de) |
| CH (1) | CH642349A5 (de) |
| DE (1) | DE2844353C2 (de) |
| DK (1) | DK146005C (de) |
| ES (1) | ES474156A1 (de) |
| FI (1) | FI70883C (de) |
| FR (1) | FR2405932A1 (de) |
| GB (1) | GB2006197B (de) |
| GR (1) | GR73919B (de) |
| IE (1) | IE47449B1 (de) |
| IL (1) | IL55695A (de) |
| IT (1) | IT1109310B (de) |
| LU (1) | LU80345A1 (de) |
| NL (1) | NL7810156A (de) |
| NO (1) | NO146161C (de) |
| PH (1) | PH15824A (de) |
| SE (1) | SE443782B (de) |
| YU (1) | YU41602B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4396629A (en) | 1980-12-29 | 1983-08-02 | Sterling Drug Inc. | Compositions, processes and method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6504268A (de) * | 1965-04-03 | 1966-10-04 | ||
| DE2551141A1 (de) * | 1975-11-14 | 1977-05-18 | Dolorgiet Arzneimittelfabrik | Cyclododecylamin-derivate |
| DE2552266A1 (de) * | 1975-11-21 | 1977-05-26 | Dolorgiet Arzneimittelfabrik | Cyclohexylamin-derivate |
-
1978
- 1978-09-26 CA CA000312115A patent/CA1116636A/en not_active Expired
- 1978-09-26 GR GR57313A patent/GR73919B/el unknown
- 1978-10-02 GB GB7838985A patent/GB2006197B/en not_active Expired
- 1978-10-04 AU AU40393/78A patent/AU520181B2/en not_active Expired
- 1978-10-04 AR AR273952A patent/AR224239A1/es active
- 1978-10-06 YU YU2352/78A patent/YU41602B/xx unknown
- 1978-10-09 IL IL55695A patent/IL55695A/xx unknown
- 1978-10-09 NL NL7810156A patent/NL7810156A/xx not_active Application Discontinuation
- 1978-10-09 FI FI783068A patent/FI70883C/fi not_active IP Right Cessation
- 1978-10-10 DK DK450978A patent/DK146005C/da not_active IP Right Cessation
- 1978-10-10 FR FR7828916A patent/FR2405932A1/fr active Granted
- 1978-10-10 IT IT51437/78A patent/IT1109310B/it active
- 1978-10-10 PH PH21691A patent/PH15824A/en unknown
- 1978-10-10 LU LU80345A patent/LU80345A1/xx unknown
- 1978-10-10 IE IE2018/78A patent/IE47449B1/en unknown
- 1978-10-10 SE SE7810574A patent/SE443782B/sv not_active IP Right Cessation
- 1978-10-10 NO NO783416A patent/NO146161C/no unknown
- 1978-10-11 ES ES474156A patent/ES474156A1/es not_active Expired
- 1978-10-11 JP JP53124219A patent/JPS6049188B2/ja not_active Expired
- 1978-10-11 DE DE2844353A patent/DE2844353C2/de not_active Expired
- 1978-10-11 CH CH1056478A patent/CH642349A5/de not_active IP Right Cessation
-
1979
- 1979-10-31 AR AR278713A patent/AR223016A1/es active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |