CA1131621A - N.sup.2-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof - Google Patents
N.sup.2-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereofInfo
- Publication number
- CA1131621A CA1131621A CA293,199A CA293199A CA1131621A CA 1131621 A CA1131621 A CA 1131621A CA 293199 A CA293199 A CA 293199A CA 1131621 A CA1131621 A CA 1131621A
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- alkoxy
- substituted
- aralkyl
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 66
- -1 furfuryl Chemical group 0.000 claims description 844
- 125000003545 alkoxy group Chemical group 0.000 claims description 214
- 125000001424 substituent group Chemical group 0.000 claims description 190
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 163
- 239000000203 mixture Substances 0.000 claims description 154
- 229910052739 hydrogen Inorganic materials 0.000 claims description 153
- 239000001257 hydrogen Substances 0.000 claims description 153
- 125000004432 carbon atom Chemical group C* 0.000 claims description 151
- 125000005843 halogen group Chemical group 0.000 claims description 116
- 150000002431 hydrogen Chemical group 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 96
- 125000001188 haloalkyl group Chemical group 0.000 claims description 87
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 82
- 125000003282 alkyl amino group Chemical group 0.000 claims description 79
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 77
- 125000004414 alkyl thio group Chemical group 0.000 claims description 74
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 73
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 71
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 71
- 125000004442 acylamino group Chemical group 0.000 claims description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 63
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 62
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 62
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 61
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 57
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 230000008569 process Effects 0.000 claims description 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 50
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 50
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 45
- 125000001624 naphthyl group Chemical group 0.000 claims description 36
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 32
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 31
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 26
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 18
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 18
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 125000005493 quinolyl group Chemical group 0.000 claims description 17
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 17
- 125000000850 2H-chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 16
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 15
- 125000005605 benzo group Chemical group 0.000 claims description 15
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 15
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 15
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 14
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 14
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 14
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 13
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 13
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 13
- 125000005561 phenanthryl group Chemical group 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 12
- 230000003301 hydrolyzing effect Effects 0.000 claims description 12
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 10
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 125000003828 azulenyl group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002192 heptalenyl group Chemical group 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001819 4H-chromenyl group Chemical group O1C(=CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 claims description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 5
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 5
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 167
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 99
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 53
- 238000004519 manufacturing process Methods 0.000 claims 11
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 abstract description 6
- 241000124008 Mammalia Species 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 230000001629 suppression Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 30
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 15
- 229960001701 chloroform Drugs 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 9
- ULEBESPCVWBNIF-BYPYZUCNSA-N L-arginine amide Chemical compound NC(=O)[C@@H](N)CCCNC(N)=N ULEBESPCVWBNIF-BYPYZUCNSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 125000005997 bromomethyl group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000004663 dialkyl amino group Chemical group 0.000 description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 7
- 241000820057 Ithone Species 0.000 description 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 7
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
- 230000015271 coagulation Effects 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229960004072 thrombin Drugs 0.000 description 7
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 108090000190 Thrombin Proteins 0.000 description 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 108010049003 Fibrinogen Proteins 0.000 description 5
- 102000008946 Fibrinogen Human genes 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 5
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 229940012952 fibrinogen Drugs 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229930064664 L-arginine Natural products 0.000 description 4
- 235000014852 L-arginine Nutrition 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 239000008279 sol Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 1
- OXQLWLOTWSOXAM-UHFFFAOYSA-M sodium;3-butoxy-2,4-dimethoxybenzenesulfonate Chemical compound [Na+].CCCCOC1=C(OC)C=CC(S([O-])(=O)=O)=C1OC OXQLWLOTWSOXAM-UHFFFAOYSA-M 0.000 description 1
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/938,711 US4201863A (en) | 1974-11-08 | 1978-08-31 | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US06/041,419 US4258192A (en) | 1977-12-16 | 1979-05-22 | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| UA2814248A UA8371A1 (uk) | 1974-11-08 | 1979-08-30 | СПОСІБ ОДЕРЖАННЯ N2-АРІЛ-СУЛЬФОНІЛ-alРha АРГІНІНАМІДІВ |
Applications Claiming Priority (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US760,668 | 1977-01-19 | ||
| US05/760,676 US4097472A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
| US05/760,929 US4101653A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-argininamides and the pharmaceutically acceptable salts thereof |
| US760,672 | 1977-01-19 | ||
| US760,929 | 1977-01-19 | ||
| US760,676 | 1977-01-19 | ||
| US05/760,745 US4066773A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US05/760,672 US4093712A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US05/760,668 US4073913A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US760,745 | 1977-01-19 | ||
| US05/776,195 US4097591A (en) | 1974-11-08 | 1977-03-10 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| JP6650877A JPS6010028B2 (ja) | 1977-06-06 | 1977-06-06 | Ｎ↑２−アリ−ルスルホニル−ｌ−アルギニンアミド類及び薬剤として許容され得るその塩 |
| US66508/77 | 1977-06-06 | ||
| US05/804,331 US4140681A (en) | 1974-11-08 | 1977-06-07 | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US804,331 | 1977-06-07 | ||
| US804,368 | 1977-06-07 | ||
| US05/804,368 US4131673A (en) | 1974-11-08 | 1977-06-07 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US776,195 | 1985-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131621A true CA1131621A (en) | 1982-09-14 |
Family
ID=27577127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,199A Expired CA1131621A (en) | 1974-11-08 | 1977-12-16 | N.sup.2-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
Country Status (17)
| Country | Link |
|---|---|
| CA (1) | CA1131621A (xx) |
| CH (2) | CH633773A5 (xx) |
| DD (1) | DD137352A5 (xx) |
| DE (1) | DE2801478A1 (xx) |
| DK (1) | DK150521C (xx) |
| FI (1) | FI72316C (xx) |
| GB (1) | GB1596971A (xx) |
| GR (1) | GR60787B (xx) |
| IL (1) | IL53685A (xx) |
| IT (1) | IT1126229B (xx) |
| NL (1) | NL187746C (xx) |
| NO (1) | NO158681C (xx) |
| NZ (1) | NZ186198A (xx) |
| PH (1) | PH15913A (xx) |
| SE (1) | SE452624B (xx) |
| SU (1) | SU1181539A3 (xx) |
| UA (1) | UA8370A1 (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT4368B (lt) | 1994-12-22 | 1998-08-25 | Biochem Pharma Inc. | Mažos molekulinės masės bicikliniai trombino inhibitoriai |
| US6057314A (en) * | 1995-12-21 | 2000-05-02 | Biochem Pharma Inc. | Low molecular weight bicyclic thrombin inhibitors |
| CN111961114A (zh) * | 2020-08-03 | 2020-11-20 | 扬州中宝药业股份有限公司 | 一种阿加曲班中间体及其制备方法与应用 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE48623B1 (en) * | 1978-08-31 | 1985-03-20 | Mitsubishi Chem Ind | Alpha-(n-arylsulfonyl-l-argininamides,processes for their preparation and pharmaceutical compositions containing these substances |
| ZA794581B (en) * | 1978-08-31 | 1981-04-29 | Mitsubishi Chem Ind | N 2-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
| GB9209032D0 (en) * | 1992-04-25 | 1992-06-10 | Ciba Geigy Ag | New peptide derivatives |
| FR2761065B1 (fr) * | 1997-03-20 | 2000-03-03 | Synthelabo | Derives de n-(arginyle)benzenesulfonamide, leur preparation et leur application en therapeutique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978045A (en) * | 1973-08-13 | 1976-08-31 | Mitsubishi Chemical Industries Ltd. | N2 -dansyl-L-arginine derivatives, and the pharmaceutically acceptable acid addition salts thereof |
-
1977
- 1977-12-16 CA CA293,199A patent/CA1131621A/en not_active Expired
- 1977-12-23 IL IL53685A patent/IL53685A/xx unknown
- 1977-12-27 IT IT31297/77A patent/IT1126229B/it active
-
1978
- 1978-01-10 FI FI780073A patent/FI72316C/fi not_active IP Right Cessation
- 1978-01-11 NZ NZ186198A patent/NZ186198A/xx unknown
- 1978-01-13 NL NLAANVRAGE7800448,A patent/NL187746C/xx not_active IP Right Cessation
- 1978-01-13 DE DE19782801478 patent/DE2801478A1/de active Granted
- 1978-01-13 PH PH20660A patent/PH15913A/en unknown
- 1978-01-17 SE SE7800512A patent/SE452624B/sv not_active IP Right Cessation
- 1978-01-18 NO NO780191A patent/NO158681C/no unknown
- 1978-01-18 GB GB2063/78A patent/GB1596971A/en not_active Expired
- 1978-01-18 CH CH51978A patent/CH633773A5/de not_active IP Right Cessation
- 1978-01-18 UA UA2776611A patent/UA8370A1/uk unknown
- 1978-01-18 SU SU782566652A patent/SU1181539A3/ru active
- 1978-01-18 DK DK026378A patent/DK150521C/da not_active IP Right Cessation
- 1978-01-18 CH CH4530/82A patent/CH648293A5/de not_active IP Right Cessation
- 1978-01-18 GR GR55191A patent/GR60787B/el unknown
- 1978-01-19 DD DD78203302A patent/DD137352A5/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT4368B (lt) | 1994-12-22 | 1998-08-25 | Biochem Pharma Inc. | Mažos molekulinės masės bicikliniai trombino inhibitoriai |
| US6057314A (en) * | 1995-12-21 | 2000-05-02 | Biochem Pharma Inc. | Low molecular weight bicyclic thrombin inhibitors |
| CN111961114A (zh) * | 2020-08-03 | 2020-11-20 | 扬州中宝药业股份有限公司 | 一种阿加曲班中间体及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL187746C (nl) | 1992-01-02 |
| DE2801478C2 (xx) | 1991-01-31 |
| CH648293A5 (en) | 1985-03-15 |
| UA8370A1 (uk) | 1996-03-29 |
| IL53685A (en) | 1985-12-31 |
| DD137352A5 (de) | 1979-08-29 |
| FI72316C (fi) | 1987-05-11 |
| IL53685A0 (en) | 1978-03-10 |
| DK150521C (da) | 1987-10-19 |
| NO158681C (no) | 1988-10-19 |
| PH15913A (en) | 1983-04-22 |
| GB1596971A (en) | 1981-09-03 |
| FI780073A (fi) | 1978-07-20 |
| GR60787B (en) | 1978-08-28 |
| SE452624B (sv) | 1987-12-07 |
| SE7800512L (sv) | 1978-07-20 |
| NO780191L (no) | 1978-07-20 |
| DK26378A (da) | 1978-07-20 |
| FI72316B (fi) | 1987-01-30 |
| IT1126229B (it) | 1986-05-14 |
| DE2801478A1 (de) | 1978-07-20 |
| NL187746B (nl) | 1991-08-01 |
| SU1181539A3 (ru) | 1985-09-23 |
| DK150521B (da) | 1987-03-16 |
| CH633773A5 (en) | 1982-12-31 |
| NZ186198A (en) | 1980-12-19 |
| NO158681B (no) | 1988-07-11 |
| NL7800448A (nl) | 1978-07-21 |
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