CH620667A5 - - Google Patents
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- Publication number
- CH620667A5 CH620667A5 CH295675A CH295675A CH620667A5 CH 620667 A5 CH620667 A5 CH 620667A5 CH 295675 A CH295675 A CH 295675A CH 295675 A CH295675 A CH 295675A CH 620667 A5 CH620667 A5 CH 620667A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- sodium
- hcl
- acid
- Prior art date
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- -1 alkyl radicals Chemical class 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 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 19
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- YFESOSRPNPYODN-RSMWSHJLSA-N (2s,3s,4s,5r,6r)-6-[[(4s,6ar,6bs,8r,8ar,9r,10r,14br)-9-acetyloxy-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2s,3r,4s, Chemical compound O([C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)OC1CC[C@]2(C)C3CC=C4[C@@]([C@@]3(CCC2[C@]1(CO)C)C)(C)C[C@@H](O)[C@@]1(CO)[C@@H](OC(C)=O)[C@@H](C(CC14)(C)C)OC(=O)C(\C)=C/C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.O([C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)OC1CC[C@]2(C)C3CC=C4[C@@]([C@@]3(CCC2[C@]1(CO)C)C)(C)C[C@@H](O)[C@@]1(CO)[C@@H](OC(C)=O)[C@@H](C(CC14)(C)C)OC(=O)C(/C)=C/C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YFESOSRPNPYODN-RSMWSHJLSA-N 0.000 description 7
- LREQLEBVOXIEOM-UHFFFAOYSA-N 6-amino-2-methyl-2-heptanol Chemical compound CC(N)CCCC(C)(C)O LREQLEBVOXIEOM-UHFFFAOYSA-N 0.000 description 7
- AXNVHPCVMSNXNP-GKTCLTPXSA-N Aescin Natural products O=C(O[C@H]1[C@@H](OC(=O)C)[C@]2(CO)[C@@H](O)C[C@@]3(C)[C@@]4(C)[C@@H]([C@]5(C)[C@H]([C@](CO)(C)[C@@H](O[C@@H]6[C@@H](O[C@H]7[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)[C@@H](O)[C@H](O[C@H]7[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O7)[C@@H](C(=O)O)O6)CC5)CC4)CC=C3[C@@H]2CC1(C)C)/C(=C/C)/C AXNVHPCVMSNXNP-GKTCLTPXSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 240000007711 Peperomia pellucida Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 229960005402 heptaminol Drugs 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 210000003462 vein Anatomy 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 5
- WMJQUHZJDDSENQ-UHFFFAOYSA-N 2-[(2,4,6-trimethylphenyl)methyl]heptan-1-amine Chemical compound CCCCCC(CN)CC1=C(C)C=C(C)C=C1C WMJQUHZJDDSENQ-UHFFFAOYSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 210000003240 portal vein Anatomy 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 208000024780 Urticaria Diseases 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000003501 anti-edematous effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 230000000304 vasodilatating effect Effects 0.000 description 3
- UNRGEIXQCZHICP-UHFFFAOYSA-N 2-(chloromethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(CCl)C(C)=C1 UNRGEIXQCZHICP-UHFFFAOYSA-N 0.000 description 2
- GVLZVUHGZRIELX-UHFFFAOYSA-N 2-[(2,4,6-trimethylphenyl)methyl]heptan-1-amine;hydrochloride Chemical compound Cl.CCCCCC(CN)CC1=C(C)C=C(C)C=C1C GVLZVUHGZRIELX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010047139 Vasoconstriction Diseases 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 150000003974 aralkylamines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000004856 capillary permeability Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VACOMSNNWGXHSF-UHFFFAOYSA-N chloro(dimethylphosphoryl)methane Chemical compound CP(C)(=O)CCl VACOMSNNWGXHSF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LRCXRAABFLIVAI-UHFFFAOYSA-N norfenefrine Chemical compound NCC(O)C1=CC=CC(O)=C1 LRCXRAABFLIVAI-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 230000025033 vasoconstriction Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- WELJYWXFTXSTBL-UHFFFAOYSA-N (2,3,5,6-tetramethylphenyl)methanamine Chemical compound CC1=CC(C)=C(C)C(CN)=C1C WELJYWXFTXSTBL-UHFFFAOYSA-N 0.000 description 1
- DGSRAILDFBJNQI-UHFFFAOYSA-N (2,4,6-trimethylphenyl)methanamine Chemical compound CC1=CC(C)=C(CN)C(C)=C1 DGSRAILDFBJNQI-UHFFFAOYSA-N 0.000 description 1
- VLVLNNQMURDGPM-UHFFFAOYSA-N (2,6-dichlorophenyl)methanamine Chemical compound NCC1=C(Cl)C=CC=C1Cl VLVLNNQMURDGPM-UHFFFAOYSA-N 0.000 description 1
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
- LXEWDLHLSPNBCR-UHFFFAOYSA-N (3,4,5-trimethylphenyl)methanamine Chemical compound CC1=CC(CN)=CC(C)=C1C LXEWDLHLSPNBCR-UHFFFAOYSA-N 0.000 description 1
- SUYJXERPRICYRX-UHFFFAOYSA-N (3-bromophenyl)methanamine Chemical compound NCC1=CC=CC(Br)=C1 SUYJXERPRICYRX-UHFFFAOYSA-N 0.000 description 1
- BJFPYGGTDAYECS-UHFFFAOYSA-N (3-chlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1 BJFPYGGTDAYECS-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 1
- KRMASLIGIOYYHM-UHFFFAOYSA-N (4-tert-butyl-2,6-dimethylphenyl)methanamine Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1CN KRMASLIGIOYYHM-UHFFFAOYSA-N 0.000 description 1
- JZFPPHPCYYGTKH-UHFFFAOYSA-N (5-tert-butyl-2-methylphenyl)methanamine Chemical compound CC1=CC=C(C(C)(C)C)C=C1CN JZFPPHPCYYGTKH-UHFFFAOYSA-N 0.000 description 1
- JDTPCYOUHSDFLR-UHFFFAOYSA-N 1-(3-chloropropoxy)hexane Chemical compound CCCCCCOCCCCl JDTPCYOUHSDFLR-UHFFFAOYSA-N 0.000 description 1
- YHMFTAUOYLECGZ-UHFFFAOYSA-N 1-(chloromethyl)-2,4,5-trimethylbenzene Chemical compound CC1=CC(C)=C(CCl)C=C1C YHMFTAUOYLECGZ-UHFFFAOYSA-N 0.000 description 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
- UDKGXKYEWBGQCG-UHFFFAOYSA-N 1-bromo-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Br)=C1 UDKGXKYEWBGQCG-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
- AQVWVFMAJAIJFG-UHFFFAOYSA-N 1-chloro-3-ethoxypropane Chemical compound CCOCCCCl AQVWVFMAJAIJFG-UHFFFAOYSA-N 0.000 description 1
- OYVDATWIUMMRMU-UHFFFAOYSA-N 1-chloro-3-propan-2-yloxypropane Chemical compound CC(C)OCCCCl OYVDATWIUMMRMU-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- PMIZBAFAPJAEAP-UHFFFAOYSA-N 1-phenyl-2-(2,4,6-trimethylphenyl)ethanesulfonic acid Chemical compound CC1=C(CC(C2=CC=CC=C2)S(=O)(=O)O)C(=CC(=C1)C)C PMIZBAFAPJAEAP-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- HOHUHSDPKVDSGC-UHFFFAOYSA-N 2-[(2,3,5,6-tetramethylphenyl)methyl]heptan-1-amine;hydrochloride Chemical compound Cl.CCCCCC(CN)CC1=C(C)C(C)=CC(C)=C1C HOHUHSDPKVDSGC-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- SBJACJNGROKNPT-UHFFFAOYSA-N 2-bromo-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)Br SBJACJNGROKNPT-UHFFFAOYSA-N 0.000 description 1
- HLAUCEOFCOXKNF-UHFFFAOYSA-N 2-bromoheptane Chemical compound CCCCCC(C)Br HLAUCEOFCOXKNF-UHFFFAOYSA-N 0.000 description 1
- JPFZKJQZKBEPGQ-UHFFFAOYSA-N 2-chloro-3-methylpentane Chemical compound CCC(C)C(C)Cl JPFZKJQZKBEPGQ-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- NKGYBXHAQAKSSG-UHFFFAOYSA-N iproheptine Chemical compound CC(C)CCCC(C)NC(C)C NKGYBXHAQAKSSG-UHFFFAOYSA-N 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- YAHRDLICUYEDAU-UHFFFAOYSA-N methylhexaneamine Chemical compound CCC(C)CC(C)N YAHRDLICUYEDAU-UHFFFAOYSA-N 0.000 description 1
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- ISPPHJQCJFEUGK-UHFFFAOYSA-N n-(2-cyclohexylethyl)hexan-1-amine Chemical compound CCCCCCNCCC1CCCCC1 ISPPHJQCJFEUGK-UHFFFAOYSA-N 0.000 description 1
- FQPKCBUXMZDHSH-UHFFFAOYSA-N n-[(2,3,5,6-tetramethylphenyl)methyl]heptan-2-amine Chemical compound CCCCCC(C)NCC1=C(C)C(C)=CC(C)=C1C FQPKCBUXMZDHSH-UHFFFAOYSA-N 0.000 description 1
- ZLVOFPSPMOLPJY-UHFFFAOYSA-N n-[(2,4,6-trimethylphenyl)methyl]heptan-2-amine Chemical compound CCCCCC(C)NCC1=C(C)C=C(C)C=C1C ZLVOFPSPMOLPJY-UHFFFAOYSA-N 0.000 description 1
- BGWFQRDYRSCOCO-UHFFFAOYSA-N n-methylheptan-2-amine Chemical compound CCCCCC(C)NC BGWFQRDYRSCOCO-UHFFFAOYSA-N 0.000 description 1
- NRHFCVZHOXLLNL-UHFFFAOYSA-N n-propylheptan-2-amine Chemical compound CCCCCC(C)NCCC NRHFCVZHOXLLNL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ALXIFCUEJWCQQL-UHFFFAOYSA-N nonan-2-amine Chemical compound CCCCCCCC(C)N ALXIFCUEJWCQQL-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
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- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-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
- JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical class CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008030 superplasticizer Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742411406 DE2411406C3 (de) | 1974-03-09 | 1974-03-09 | Benzylalkylamine und Verfahren zu ihrer Herstellung |
| DE2428625A DE2428625A1 (de) | 1974-06-14 | 1974-06-14 | Aralkylamine und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620667A5 true CH620667A5 (ja) | 1980-12-15 |
Family
ID=25766761
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH295675A CH620667A5 (ja) | 1974-03-09 | 1975-03-07 | |
| CH105880A CH623561A5 (ja) | 1974-03-09 | 1980-02-08 | |
| CH105980A CH628018A5 (de) | 1974-03-09 | 1980-02-08 | Verfahren zur herstellung von aralkylaminen. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH105880A CH623561A5 (ja) | 1974-03-09 | 1980-02-08 | |
| CH105980A CH628018A5 (de) | 1974-03-09 | 1980-02-08 | Verfahren zur herstellung von aralkylaminen. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4312861A (ja) |
| JP (3) | JPS585181B2 (ja) |
| AT (5) | AT336567B (ja) |
| BE (1) | BE826351A (ja) |
| CH (3) | CH620667A5 (ja) |
| DK (1) | DK146851C (ja) |
| FR (1) | FR2274286A1 (ja) |
| GB (1) | GB1489306A (ja) |
| IE (1) | IE40727B1 (ja) |
| LU (1) | LU72006A1 (ja) |
| NL (1) | NL7502795A (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR75153B (ja) * | 1981-03-27 | 1984-07-13 | Lilly Co Eli | |
| US4405582A (en) * | 1982-01-18 | 1983-09-20 | Exxon Research And Engineering Co. | Process for selective removal of H2 S from mixtures containing H22 using diaminoether solutions |
| JPH026065U (ja) * | 1988-06-27 | 1990-01-16 | ||
| US5086073A (en) * | 1989-06-02 | 1992-02-04 | John Wyeth & Brother Limited | Composition for treating depression with aralkyl amines |
| DE10014127A1 (de) * | 2000-03-22 | 2001-10-18 | Hassan Jomaa | Verwendung von phosphororganischen Verbindungen zur Behandlung von Infektionen |
| US20100041622A1 (en) * | 2008-08-13 | 2010-02-18 | Bromley Philip J | Compositions containing aminoalkanes and aminoalkane derivatives |
| US9351517B2 (en) | 2013-03-15 | 2016-05-31 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and compositions containing same |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2732403A (en) * | 1956-01-24 | Chclj | ||
| US2732402A (en) * | 1956-01-24 | Chjchjoh | ||
| US2229187A (en) * | 1937-07-21 | 1941-01-21 | Sandoz Ltd | Amino-alcohol and a process for its production |
| FR961832A (ja) * | 1943-03-20 | 1950-05-23 | ||
| US2608584A (en) * | 1947-03-19 | 1952-08-26 | Nopco Chem Co | Preparation of n-alkyl arylamines |
| US2613226A (en) * | 1951-01-05 | 1952-10-07 | Rohm & Haas | Benzyl-tert.-octylamine |
| US2852562A (en) * | 1954-02-19 | 1958-09-16 | Sterling Drug Inc | Nu-hydrocarbyloxyalkyl-aralkylamines |
| CH336065A (de) * | 1954-03-05 | 1959-02-15 | Ciba Geigy | Verfahren zur Herstellung von neuen Stickstoff und Phosphor enthaltenden Verbindungen |
| US2862967A (en) * | 1955-12-09 | 1958-12-02 | Sterling Drug Inc | N-alkyl-n-(alkylated-benzyl)dihaloacetamides and preparation thereof |
| US2999872A (en) * | 1958-03-06 | 1961-09-12 | Rohm & Haas | Metal salt aminoalcohol complexes |
| DE1173649B (de) * | 1963-02-15 | 1964-07-09 | Bayer Ag | Verfahren zur Herstellung von flammwidrigen, gegebenenfalls verschaeumten Kunststoffen nach dem Polyisocyanatadditionsverfahren |
| NL129966C (ja) * | 1963-10-14 | |||
| US3406024A (en) * | 1965-08-27 | 1968-10-15 | Velsicol Chemical Corp | Method for the control of weeds |
-
1975
- 1975-03-03 IE IE449/75A patent/IE40727B1/xx unknown
- 1975-03-06 BE BE154053A patent/BE826351A/xx not_active IP Right Cessation
- 1975-03-07 CH CH295675A patent/CH620667A5/de not_active IP Right Cessation
- 1975-03-07 LU LU72006A patent/LU72006A1/xx unknown
- 1975-03-07 GB GB9632/75A patent/GB1489306A/en not_active Expired
- 1975-03-07 JP JP50027215A patent/JPS585181B2/ja not_active Expired
- 1975-03-07 FR FR7507168A patent/FR2274286A1/fr active Granted
- 1975-03-07 DK DK93275A patent/DK146851C/da not_active IP Right Cessation
- 1975-03-08 NL NL7502795A patent/NL7502795A/xx not_active Application Discontinuation
- 1975-04-25 AT AT321475A patent/AT336567B/de not_active IP Right Cessation
-
1976
- 1976-02-02 AT AT70376A patent/AT336569B/de not_active IP Right Cessation
- 1976-02-02 AT AT70476A patent/AT337666B/de not_active IP Right Cessation
- 1976-02-02 AT AT70676A patent/AT336570B/de not_active IP Right Cessation
- 1976-05-21 AT AT373576A patent/AT336571B/de not_active IP Right Cessation
-
1977
- 1977-06-13 US US05/806,272 patent/US4312861A/en not_active Expired - Lifetime
-
1978
- 1978-10-13 JP JP12525378A patent/JPS54138528A/ja active Pending
- 1978-10-13 JP JP12525278A patent/JPS54138534A/ja active Pending
-
1980
- 1980-02-08 CH CH105880A patent/CH623561A5/de not_active IP Right Cessation
- 1980-02-08 CH CH105980A patent/CH628018A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54138528A (en) | 1979-10-27 |
| DK93275A (ja) | 1975-09-10 |
| NL7502795A (nl) | 1975-09-11 |
| AT336567B (de) | 1977-05-10 |
| ATA321475A (de) | 1976-09-15 |
| FR2274286A1 (fr) | 1976-01-09 |
| AT337666B (de) | 1977-07-11 |
| JPS50123631A (ja) | 1975-09-29 |
| FR2274286B1 (ja) | 1978-08-04 |
| CH628018A5 (de) | 1982-02-15 |
| GB1489306A (en) | 1977-10-19 |
| DK146851C (da) | 1984-07-02 |
| AT336570B (de) | 1977-05-10 |
| US4312861A (en) | 1982-01-26 |
| ATA70676A (de) | 1976-09-15 |
| JPS585181B2 (ja) | 1983-01-29 |
| IE40727B1 (en) | 1979-08-01 |
| ATA373576A (de) | 1976-09-15 |
| BE826351A (fr) | 1975-09-08 |
| CH623561A5 (ja) | 1981-06-15 |
| IE40727L (en) | 1975-09-09 |
| AT336569B (de) | 1977-05-10 |
| DK146851B (da) | 1984-01-23 |
| ATA70376A (de) | 1976-09-15 |
| JPS54138534A (en) | 1979-10-27 |
| ATA70476A (de) | 1976-11-15 |
| LU72006A1 (ja) | 1976-02-04 |
| AT336571B (de) | 1977-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |