NO751779L - - Google Patents
Info
- Publication number
- NO751779L NO751779L NO751779A NO751779A NO751779L NO 751779 L NO751779 L NO 751779L NO 751779 A NO751779 A NO 751779A NO 751779 A NO751779 A NO 751779A NO 751779 L NO751779 L NO 751779L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- thienylthio
- acid
- substituents
- theoretical
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 halogen ester Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003577 thiophenes Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 235000021588 free fatty acids Nutrition 0.000 description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 20
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 239000011593 sulfur Substances 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 18
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 18
- 210000002966 serum Anatomy 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 230000004130 lipolysis Effects 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- WSMQKESQZFQMFW-UHFFFAOYSA-N 5-methyl-pyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1 WSMQKESQZFQMFW-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 206010012601 diabetes mellitus Diseases 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 150000002168 ethanoic acid esters Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 102000004877 Insulin Human genes 0.000 description 5
- 108090001061 Insulin Proteins 0.000 description 5
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 5
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 229940125396 insulin Drugs 0.000 description 5
- AOCJNPACAZCBCY-UHFFFAOYSA-N n-hydroxy-2-thiophen-2-ylsulfanylacetamide Chemical compound ONC(=O)CSC1=CC=CS1 AOCJNPACAZCBCY-UHFFFAOYSA-N 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- BNMPIJWVMVNSRD-UHFFFAOYSA-N 5-methyl-1,2-oxazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NO1 BNMPIJWVMVNSRD-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960001171 acetohydroxamic acid Drugs 0.000 description 4
- 150000003835 adenosine derivatives Chemical class 0.000 description 4
- 210000000577 adipose tissue Anatomy 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- OKEHURCMYKPVFW-UHFFFAOYSA-N 2-methoxythiophene Chemical compound COC1=CC=CS1 OKEHURCMYKPVFW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IHFXZROPBCBLLG-UHFFFAOYSA-N 2,5-dibromo-3-methylthiophene Chemical compound CC=1C=C(Br)SC=1Br IHFXZROPBCBLLG-UHFFFAOYSA-N 0.000 description 2
- SWVLAEOHFCYSJY-UHFFFAOYSA-N 2-(3,4-dimethylthiophen-2-yl)sulfanylacetonitrile Chemical compound CC1=CSC(SCC#N)=C1C SWVLAEOHFCYSJY-UHFFFAOYSA-N 0.000 description 2
- QKTCMPVZCDYGBJ-UHFFFAOYSA-N 2-(5-methoxythiophen-2-yl)sulfanylacetonitrile Chemical compound COC1=CC=C(SCC#N)S1 QKTCMPVZCDYGBJ-UHFFFAOYSA-N 0.000 description 2
- BZOFVLYZFOAVIV-UHFFFAOYSA-N 2-(5-methylthiophen-2-yl)sulfanylacetonitrile Chemical compound CC1=CC=C(SCC#N)S1 BZOFVLYZFOAVIV-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 2
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 2
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 206010043087 Tachyphylaxis Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000003243 anti-lipolytic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002545 isoxazoles Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000012153 long-term therapy Methods 0.000 description 2
- KNAYLBUYNNJTFF-UHFFFAOYSA-N methyl 2-(4-methylthiophen-2-yl)sulfanylacetate Chemical compound COC(=O)CSC1=CC(C)=CS1 KNAYLBUYNNJTFF-UHFFFAOYSA-N 0.000 description 2
- 210000000663 muscle cell Anatomy 0.000 description 2
- 230000009038 pharmacological inhibition Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- SKDNDSLDRLEELJ-UHFFFAOYSA-N 2,3,5-tribromothiophene Chemical compound BrC1=CC(Br)=C(Br)S1 SKDNDSLDRLEELJ-UHFFFAOYSA-N 0.000 description 1
- FGYBDASKYMSNCX-UHFFFAOYSA-N 2,5-dichlorothiophene Chemical compound ClC1=CC=C(Cl)S1 FGYBDASKYMSNCX-UHFFFAOYSA-N 0.000 description 1
- MJNUOJAOCSFMAL-UHFFFAOYSA-N 2-(3,4-dimethoxythiophen-2-yl)sulfanylacetonitrile Chemical compound COC1=CSC(SCC#N)=C1OC MJNUOJAOCSFMAL-UHFFFAOYSA-N 0.000 description 1
- FFEIZXOMJHELKD-UHFFFAOYSA-N 2-(3,5-dibromothiophen-2-yl)sulfanyl-n-hydroxyacetamide Chemical compound ONC(=O)CSC=1SC(Br)=CC=1Br FFEIZXOMJHELKD-UHFFFAOYSA-N 0.000 description 1
- PJYSKWNXENCVHP-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)acetonitrile Chemical compound ClC1=CC=C(CC#N)S1 PJYSKWNXENCVHP-UHFFFAOYSA-N 0.000 description 1
- JCASQAKMLUYFRS-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)sulfanylacetonitrile Chemical compound ClC1=CC=C(SCC#N)S1 JCASQAKMLUYFRS-UHFFFAOYSA-N 0.000 description 1
- HKLZODRLQWKDLB-UHFFFAOYSA-N 2-(5-ethylthiophen-2-yl)sulfanylacetic acid Chemical compound CCC1=CC=C(SCC(O)=O)S1 HKLZODRLQWKDLB-UHFFFAOYSA-N 0.000 description 1
- PZAWQZAIIRNLOE-UHFFFAOYSA-N 2-(5-methoxythiophen-2-yl)sulfanylacetic acid Chemical compound COC1=CC=C(SCC(O)=O)S1 PZAWQZAIIRNLOE-UHFFFAOYSA-N 0.000 description 1
- CGDVQZOTWAGOPE-UHFFFAOYSA-N 2-(5-methoxythiophen-2-yl)sulfanylpropanenitrile Chemical compound COC1=CC=C(SC(C)C#N)S1 CGDVQZOTWAGOPE-UHFFFAOYSA-N 0.000 description 1
- PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 description 1
- JCCCMAAJYSNBPR-UHFFFAOYSA-N 2-ethylthiophene Chemical compound CCC1=CC=CS1 JCCCMAAJYSNBPR-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- ZUDCKLVMBAXBIF-UHFFFAOYSA-N 3,4-dimethoxythiophene Chemical compound COC1=CSC=C1OC ZUDCKLVMBAXBIF-UHFFFAOYSA-N 0.000 description 1
- GPSFYJDZKSRMKZ-UHFFFAOYSA-N 3,4-dimethylthiophene Chemical compound CC1=CSC=C1C GPSFYJDZKSRMKZ-UHFFFAOYSA-N 0.000 description 1
- FICAQKBMCKEFDI-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole Chemical compound CC=1C=C(C)ON=1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- SECHDFHDDVELCV-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)pyridine Chemical compound C1=CN=CC(C2=NNN=N2)=C1 SECHDFHDDVELCV-UHFFFAOYSA-N 0.000 description 1
- RFSKGCVUDQRZSD-UHFFFAOYSA-N 3-methoxythiophene Chemical compound COC=1C=CSC=1 RFSKGCVUDQRZSD-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- FNHVVMJBCILJGA-UHFFFAOYSA-N 4-methyl-pyrazole-3-carboxylic acid Chemical compound CC=1C=NNC=1C(O)=O FNHVVMJBCILJGA-UHFFFAOYSA-N 0.000 description 1
- VSRLRNRJJLZHPP-UHFFFAOYSA-N 5-(thiophen-2-ylsulfanylmethyl)-2h-tetrazole Chemical compound N=1N=NNC=1CSC1=CC=CS1 VSRLRNRJJLZHPP-UHFFFAOYSA-N 0.000 description 1
- JLYUHYPACRNVHH-UHFFFAOYSA-N 5-[(3,4-dimethoxythiophen-2-yl)sulfanylmethyl]-2h-tetrazole Chemical compound COC1=CSC(SCC=2NN=NN=2)=C1OC JLYUHYPACRNVHH-UHFFFAOYSA-N 0.000 description 1
- CQPGFZHVKXKHAP-UHFFFAOYSA-N 5-[(5-chlorothiophen-2-yl)sulfanylmethyl]-2h-tetrazole Chemical compound S1C(Cl)=CC=C1SCC1=NN=NN1 CQPGFZHVKXKHAP-UHFFFAOYSA-N 0.000 description 1
- TZQSDVUJKBIUMU-UHFFFAOYSA-N 5-[1-(5-methoxythiophen-2-yl)sulfanylethyl]-2h-tetrazole Chemical compound S1C(OC)=CC=C1SC(C)C1=NN=NN1 TZQSDVUJKBIUMU-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- YJRGMUWRPCPLNH-UHFFFAOYSA-N butyl 2-chloroacetate Chemical compound CCCCOC(=O)CCl YJRGMUWRPCPLNH-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- BPOKPXVWCPYDPO-UHFFFAOYSA-N ethyl 2-thiophen-2-ylsulfanylpropanoate Chemical compound CCOC(=O)C(C)SC1=CC=CS1 BPOKPXVWCPYDPO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000004190 glucose uptake Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CRXKOALCSUKHBZ-UHFFFAOYSA-N methyl 2-(5-ethylthiophen-2-yl)sulfanylacetate Chemical compound COC(CSC=1SC(=CC1)CC)=O CRXKOALCSUKHBZ-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- ABMWEAZOQNRCJA-UHFFFAOYSA-N methyl 2-thiophen-3-ylsulfanylacetate Chemical compound COC(=O)CSC=1C=CSC=1 ABMWEAZOQNRCJA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QVOBHZDXDMJIMR-UHFFFAOYSA-N n-hydroxy-2-(5-methoxythiophen-2-yl)sulfanylacetamide Chemical compound COC1=CC=C(SCC(=O)NO)S1 QVOBHZDXDMJIMR-UHFFFAOYSA-N 0.000 description 1
- XSVOKPWCLLWLCX-UHFFFAOYSA-N n-hydroxy-2-thiophen-2-ylsulfanylpentanamide Chemical compound CCCC(C(=O)NO)SC1=CC=CS1 XSVOKPWCLLWLCX-UHFFFAOYSA-N 0.000 description 1
- LVVVBWIVLBJGLP-UHFFFAOYSA-N n-hydroxy-2-thiophen-3-ylsulfanylacetamide Chemical compound ONC(=O)CSC=1C=CSC=1 LVVVBWIVLBJGLP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002129 tachyphylactic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2424742A DE2424742C3 (de) | 1974-05-21 | 1974-05-21 | Thiophenderivate Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751779L true NO751779L (enExample) | 1975-11-24 |
Family
ID=5916183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751779A NO751779L (enExample) | 1974-05-21 | 1975-05-20 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4031236A (enExample) |
| JP (1) | JPS50160267A (enExample) |
| AT (1) | ATA385775A (enExample) |
| AU (1) | AU8138475A (enExample) |
| BE (1) | BE829307A (enExample) |
| DD (1) | DD121111A5 (enExample) |
| DE (1) | DE2424742C3 (enExample) |
| DK (1) | DK136366C (enExample) |
| ES (1) | ES437803A1 (enExample) |
| FI (1) | FI751474A7 (enExample) |
| FR (1) | FR2271816A1 (enExample) |
| GB (1) | GB1512236A (enExample) |
| IL (1) | IL47291A0 (enExample) |
| NL (1) | NL7505571A (enExample) |
| NO (1) | NO751779L (enExample) |
| SE (1) | SE7505711L (enExample) |
| ZA (1) | ZA753296B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2464953A1 (fr) * | 1979-09-06 | 1981-03-20 | Sanofi Sa | Derives d'a-(thienyl-2 thio) phenylacetamides, leur procede de preparation et leur application therapeutique |
| ES8505199A1 (es) * | 1982-10-21 | 1985-05-16 | Lilly Industries Ltd | Un procedimiento para la preparacion de derivados de difenilalquilenicos. |
| US4885355A (en) * | 1982-12-09 | 1989-12-05 | The Dow Chemical Company | Water-insoluble polymers from cyclic sulfonium compounds |
| GB8725260D0 (en) * | 1987-10-28 | 1987-12-02 | Lilly Industries Ltd | Organic compounds |
| US6172057B1 (en) | 1997-02-27 | 2001-01-09 | American Cyanamid Company | N-Hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
| EA001742B1 (ru) * | 1997-02-27 | 2001-08-27 | Американ Цианамид Компани | N-гидрокси-2-(алкил-, арил- или гетероарилсульфанил, -сульфинил или -сульфонил)-3-замещенные алкилов, арилов или гетероариламидов в качестве ингибиторов матриксных металлопротеиназ |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2581626A (en) * | 1948-10-06 | 1952-01-08 | Socony Vacuum Oil Co Inc | Thienylthio carboxylic acids and thienylthio carboxylic acid esters in lubricating compositions |
| US3560525A (en) * | 1967-10-13 | 1971-02-02 | Parke Davis & Co | 5-phenyl-2-furanacetic acids,5-phenyl-2-thiopheneacetic acids,and their derivatives |
-
1974
- 1974-05-21 DE DE2424742A patent/DE2424742C3/de not_active Expired
-
1975
- 1975-05-13 NL NL7505571A patent/NL7505571A/xx unknown
- 1975-05-14 IL IL47291A patent/IL47291A0/xx unknown
- 1975-05-20 ES ES437803A patent/ES437803A1/es not_active Expired
- 1975-05-20 SE SE7505711A patent/SE7505711L/xx unknown
- 1975-05-20 DD DD186142A patent/DD121111A5/xx unknown
- 1975-05-20 US US05/579,258 patent/US4031236A/en not_active Expired - Lifetime
- 1975-05-20 FI FI751474A patent/FI751474A7/fi not_active Application Discontinuation
- 1975-05-20 NO NO751779A patent/NO751779L/no unknown
- 1975-05-21 BE BE156549A patent/BE829307A/xx unknown
- 1975-05-21 AT AT753857A patent/ATA385775A/de not_active IP Right Cessation
- 1975-05-21 GB GB21972/75A patent/GB1512236A/en not_active Expired
- 1975-05-21 FR FR7515772A patent/FR2271816A1/fr not_active Withdrawn
- 1975-05-21 ZA ZA00753296A patent/ZA753296B/xx unknown
- 1975-05-21 DK DK224175A patent/DK136366C/da active
- 1975-05-21 JP JP50060837A patent/JPS50160267A/ja active Pending
- 1975-05-21 AU AU81384/75A patent/AU8138475A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI751474A7 (enExample) | 1975-11-22 |
| DE2424742A1 (de) | 1975-12-04 |
| AU8138475A (en) | 1976-11-25 |
| DK224175A (da) | 1975-11-22 |
| DD121111A5 (enExample) | 1976-07-12 |
| DK136366B (da) | 1977-10-03 |
| US4031236A (en) | 1977-06-21 |
| SE7505711L (sv) | 1975-11-24 |
| ATA385775A (de) | 1978-03-15 |
| IL47291A0 (en) | 1975-07-28 |
| ES437803A1 (es) | 1977-01-01 |
| DE2424742C3 (de) | 1982-04-22 |
| DK136366C (da) | 1978-02-27 |
| DE2424742B2 (de) | 1981-02-19 |
| NL7505571A (nl) | 1975-11-25 |
| FR2271816A1 (enExample) | 1975-12-19 |
| ZA753296B (en) | 1976-04-28 |
| JPS50160267A (enExample) | 1975-12-25 |
| BE829307A (fr) | 1975-11-21 |
| GB1512236A (en) | 1978-05-24 |
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