NO782650L - Fremgangsmaate ved fremstilling av diortosubstituerte benzen-derivater - Google Patents
Fremgangsmaate ved fremstilling av diortosubstituerte benzen-derivaterInfo
- Publication number
- NO782650L NO782650L NO782650A NO782650A NO782650L NO 782650 L NO782650 L NO 782650L NO 782650 A NO782650 A NO 782650A NO 782650 A NO782650 A NO 782650A NO 782650 L NO782650 L NO 782650L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- group
- stated
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000006239 protecting group Chemical group 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 32
- 239000013078 crystal Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000011734 sodium Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 108010071289 Factor XIII Proteins 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- 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 7
- 229940012444 factor xiii Drugs 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 150000003456 sulfonamides Chemical class 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- -1 benzene compound Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 5
- 102000009123 Fibrin Human genes 0.000 description 5
- 108010073385 Fibrin Proteins 0.000 description 5
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 5
- 208000007536 Thrombosis Diseases 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 5
- 229950003499 fibrin Drugs 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 229960003151 mercaptamine Drugs 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- MLEBFEHOJICQQS-UHFFFAOYSA-N monodansylcadaverine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NCCCCCN MLEBFEHOJICQQS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FCEDUZSZDSKMJT-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-n,2,4,6-tetramethylbenzenesulfonamide Chemical compound NCCSCCN(C)S(=O)(=O)C1=C(C)C=C(C)C=C1C FCEDUZSZDSKMJT-UHFFFAOYSA-N 0.000 description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- LKUDPHPHKOZXCD-UHFFFAOYSA-N 1,3,5-trimethoxybenzene Chemical compound COC1=CC(OC)=CC(OC)=C1 LKUDPHPHKOZXCD-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 108010000196 Factor XIIIa Proteins 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 102100038103 Protein-glutamine gamma-glutamyltransferase 4 Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000003527 fibrinolytic agent Substances 0.000 description 2
- 230000003480 fibrinolytic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- KYNQHQCVJJVVRO-UHFFFAOYSA-N n-(2,4,6-trimethylphenyl)ethenesulfonamide Chemical compound CC1=CC(C)=C(NS(=O)(=O)C=C)C(C)=C1 KYNQHQCVJJVVRO-UHFFFAOYSA-N 0.000 description 2
- YHLNFLKIXOXOFE-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(=O)(=O)NCCSCCN)C(C)=C1 YHLNFLKIXOXOFE-UHFFFAOYSA-N 0.000 description 2
- QAUIGXVTPGDUQC-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,6-dimethyl-4-propan-2-ylbenzenesulfonamide Chemical compound CC(C)C1=CC(C)=C(S(=O)(=O)NCCSCCN)C(C)=C1 QAUIGXVTPGDUQC-UHFFFAOYSA-N 0.000 description 2
- 150000005002 naphthylamines Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 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
- 239000002243 precursor Substances 0.000 description 2
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- FZSPYHREEHYLCB-UHFFFAOYSA-N 1-tert-butyl-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(C(C)(C)C)=C1 FZSPYHREEHYLCB-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
- FGJGNZDVLPUDAJ-UHFFFAOYSA-N 2,4,6-trimethoxybenzenesulfonyl chloride Chemical compound COC1=CC(OC)=C(S(Cl)(=O)=O)C(OC)=C1 FGJGNZDVLPUDAJ-UHFFFAOYSA-N 0.000 description 1
- PKTPLIYCHQWVOW-UHFFFAOYSA-N 2,4,6-trimethyl-n-(2-sulfanylethyl)benzenesulfonamide Chemical compound CC1=CC(C)=C(S(=O)(=O)NCCS)C(C)=C1 PKTPLIYCHQWVOW-UHFFFAOYSA-N 0.000 description 1
- QXWAUQMMMIMLTO-UHFFFAOYSA-N 2,6-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(F)=C1S(Cl)(=O)=O QXWAUQMMMIMLTO-UHFFFAOYSA-N 0.000 description 1
- NSBSVUUVECHDDX-UHFFFAOYSA-N 2,6-dimethyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1N NSBSVUUVECHDDX-UHFFFAOYSA-N 0.000 description 1
- WFFMIEOUCQAIPX-UHFFFAOYSA-N 2,6-dimethyl-4-nitrobenzenesulfonyl chloride Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1S(Cl)(=O)=O WFFMIEOUCQAIPX-UHFFFAOYSA-N 0.000 description 1
- KVVCTEUZKMHDBN-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)-n-(2,4,6-trimethylphenyl)ethanesulfonamide Chemical compound CC1=CC(C)=C(NS(=O)(=O)CCSCCN)C(C)=C1 KVVCTEUZKMHDBN-UHFFFAOYSA-N 0.000 description 1
- QTHTVKOHFTXPIJ-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)-n-(2,6-dimethyl-4-nitrophenyl)ethanesulfonamide Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1NS(=O)(=O)CCSCCN QTHTVKOHFTXPIJ-UHFFFAOYSA-N 0.000 description 1
- DCDNGKKZBLSZTI-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)-n-methyl-n-(2,4,6-trimethylphenyl)ethanesulfonamide Chemical compound NCCSCCS(=O)(=O)N(C)C1=C(C)C=C(C)C=C1C DCDNGKKZBLSZTI-UHFFFAOYSA-N 0.000 description 1
- JONTXEXBTWSUKE-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)ethanamine Chemical compound NCCSCCN JONTXEXBTWSUKE-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- UKFTXWKNVSVVCJ-UHFFFAOYSA-N 2-[(6-hydrazinylpyridazin-3-yl)-(2-hydroxyethyl)amino]ethanol;hydron;dichloride Chemical class Cl.Cl.NNC1=CC=C(N(CCO)CCO)N=N1 UKFTXWKNVSVVCJ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MJZJRYUPMNKDQR-UHFFFAOYSA-N 2-aminoethanethiol;dihydrochloride Chemical compound Cl.Cl.NCCS MJZJRYUPMNKDQR-UHFFFAOYSA-N 0.000 description 1
- NCQGMSXDPWADQW-UHFFFAOYSA-N 3-[2-[(2,4,6-trimethylphenyl)sulfonylamino]ethylsulfanyl]propanoic acid Chemical compound CC1=CC(C)=C(S(=O)(=O)NCCSCCC(O)=O)C(C)=C1 NCQGMSXDPWADQW-UHFFFAOYSA-N 0.000 description 1
- TVJMJSHACSKREH-UHFFFAOYSA-N 3-[2-[(2,4,6-trimethylphenyl)sulfonylamino]ethylsulfanyl]propanoyl chloride Chemical compound CC1=CC(C)=C(S(=O)(=O)NCCSCCC(Cl)=O)C(C)=C1 TVJMJSHACSKREH-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- UBQPMTQKJYOWDV-UHFFFAOYSA-N bromo(chlorosulfonyloxy)methane Chemical compound ClS(=O)(=O)OCBr UBQPMTQKJYOWDV-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical class NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- SHTCBKPGCZMLOX-UHFFFAOYSA-N n-(2,6-dimethyl-4-nitrophenyl)ethenesulfonamide Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1NS(=O)(=O)C=C SHTCBKPGCZMLOX-UHFFFAOYSA-N 0.000 description 1
- COAMJDXDAAJNCS-UHFFFAOYSA-N n-(2-hydroxyethyl)-2,4,6-trimethylbenzenesulfonamide;2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1.CC1=CC(C)=C(S(=O)(=O)NCCO)C(C)=C1 COAMJDXDAAJNCS-UHFFFAOYSA-N 0.000 description 1
- KLKGYTHPUAKWTG-UHFFFAOYSA-N n-(2-hydroxyethyl)-n,2,4,6-tetramethylbenzenesulfonamide;2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1.OCCN(C)S(=O)(=O)C1=C(C)C=C(C)C=C1C KLKGYTHPUAKWTG-UHFFFAOYSA-N 0.000 description 1
- IPDULWIQFPUTMI-UHFFFAOYSA-N n-(4-amino-2,6-dimethylphenyl)-2-(2-aminoethylsulfanyl)ethanesulfonamide Chemical compound CC1=CC(N)=CC(C)=C1NS(=O)(=O)CCSCCN IPDULWIQFPUTMI-UHFFFAOYSA-N 0.000 description 1
- PNJPNQVOEQEWEW-UHFFFAOYSA-N n-(4-aminobutylsulfanyl)-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(=O)(=O)NSCCCCN)C(C)=C1 PNJPNQVOEQEWEW-UHFFFAOYSA-N 0.000 description 1
- AOXSTWLLPJNAMD-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,4,6-tri(propan-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CC(C(C)C)=C(S(=O)(=O)NCCSCCN)C(C(C)C)=C1 AOXSTWLLPJNAMD-UHFFFAOYSA-N 0.000 description 1
- KLSOYMJDMYOPED-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,6-dichlorobenzenesulfonamide Chemical compound NCCSCCNS(=O)(=O)C1=C(Cl)C=CC=C1Cl KLSOYMJDMYOPED-UHFFFAOYSA-N 0.000 description 1
- QEJCARSORGZIPY-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,6-difluorobenzenesulfonamide Chemical compound NCCSCCNS(=O)(=O)C1=C(F)C=CC=C1F QEJCARSORGZIPY-UHFFFAOYSA-N 0.000 description 1
- NEFINNULWHYSDL-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,6-dimethyl-4-nitrobenzenesulfonamide Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1S(=O)(=O)NCCSCCN NEFINNULWHYSDL-UHFFFAOYSA-N 0.000 description 1
- SVUZAVUWYMZMTD-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-2,6-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(C)=C1S(=O)(=O)NCCSCCN SVUZAVUWYMZMTD-UHFFFAOYSA-N 0.000 description 1
- XXEOFMNPDLJEQF-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-3-chloro-2,6-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(Cl)C(C)=C1S(=O)(=O)NCCSCCN XXEOFMNPDLJEQF-UHFFFAOYSA-N 0.000 description 1
- BLOPFUSHTQVARJ-UHFFFAOYSA-N n-[2-(2-aminoethylsulfanyl)ethyl]-n-ethyl-2,4,6-trimethylbenzenesulfonamide Chemical compound NCCSCCN(CC)S(=O)(=O)C1=C(C)C=C(C)C=C1C BLOPFUSHTQVARJ-UHFFFAOYSA-N 0.000 description 1
- AUDNQCHPHJIPMM-UHFFFAOYSA-N n-[2-(2-chloroethylsulfanyl)ethyl]-n,2,4,6-tetramethylbenzenesulfonamide Chemical compound ClCCSCCN(C)S(=O)(=O)C1=C(C)C=C(C)C=C1C AUDNQCHPHJIPMM-UHFFFAOYSA-N 0.000 description 1
- GKICTEVJZYQDPE-UHFFFAOYSA-N n-[2-(2-hydroxyethylsulfanyl)ethyl]-n,2,4,6-tetramethylbenzenesulfonamide Chemical compound OCCSCCN(C)S(=O)(=O)C1=C(C)C=C(C)C=C1C GKICTEVJZYQDPE-UHFFFAOYSA-N 0.000 description 1
- TWWZREQQXVDAJF-UHFFFAOYSA-N n-[2-(2-isocyanatoethylsulfanyl)ethyl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(=O)(=O)NCCSCCN=C=O)C(C)=C1 TWWZREQQXVDAJF-UHFFFAOYSA-N 0.000 description 1
- WXSBFOQMLCLEHI-UHFFFAOYSA-N n-[2-(cyanomethylsulfanyl)ethyl]-n,2,4,6-tetramethylbenzenesulfonamide Chemical compound N#CCSCCN(C)S(=O)(=O)C1=C(C)C=C(C)C=C1C WXSBFOQMLCLEHI-UHFFFAOYSA-N 0.000 description 1
- ZMNMYXNWQBCWOO-UHFFFAOYSA-N n-[2-[2-(1,3-dioxoisoindol-2-yl)ethylsulfanyl]ethyl]-n,2,4,6-tetramethylbenzenesulfonamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCSCCN(C)S(=O)(=O)C1=C(C)C=C(C)C=C1C ZMNMYXNWQBCWOO-UHFFFAOYSA-N 0.000 description 1
- RJZKMBIDARKNKT-UHFFFAOYSA-N n-ethyl-n-(2-hydroxyethyl)-2,4,6-trimethylbenzenesulfonamide;2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1.OCCN(CC)S(=O)(=O)C1=C(C)C=C(C)C=C1C RJZKMBIDARKNKT-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001918 phosphonic acid ester group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000012976 tarts Nutrition 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
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3294677 | 1977-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782650L true NO782650L (no) | 1979-02-06 |
Family
ID=10346357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782650A NO782650L (no) | 1977-08-05 | 1978-08-02 | Fremgangsmaate ved fremstilling av diortosubstituerte benzen-derivater |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4218476A (es) |
| EP (1) | EP0000826A1 (es) |
| JP (1) | JPS5444635A (es) |
| AU (1) | AU3857778A (es) |
| DK (1) | DK340178A (es) |
| ES (1) | ES472290A1 (es) |
| FI (1) | FI782383A (es) |
| IT (1) | IT1099585B (es) |
| NO (1) | NO782650L (es) |
| NZ (1) | NZ188038A (es) |
| PT (1) | PT68382A (es) |
| ZA (1) | ZA784348B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4396628A (en) * | 1981-06-18 | 1983-08-02 | The United States Of America As Represented By The Department Of Health & Human Services | Antiviral activities of dansylcadaverine and closely related compounds |
| EP0294016A3 (en) * | 1987-03-27 | 1991-06-26 | Merck & Co. Inc. | Factor xiiia inhibitor compounds useful for thrombolytic therapy |
| US4968494A (en) * | 1987-03-27 | 1990-11-06 | Merck & Co., Inc. | Methods and compositions for thrombolytic therapy |
| US5185149A (en) * | 1987-03-27 | 1993-02-09 | Merck & Co., Inc. | Methods for thrombolytic therapy |
| DE3821540A1 (de) * | 1988-06-25 | 1989-12-28 | Boehringer Mannheim Gmbh | Neue sulfonamide, verfahren zu ihrer herstellung sowie solche sulfonamide enthaltende arzneimittel |
| US5047416A (en) * | 1989-07-31 | 1991-09-10 | Merck & Co., Inc. | Triazole compounds and their use as transglutaminase inhibitors |
| US5030644A (en) * | 1989-07-31 | 1991-07-09 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5077285A (en) * | 1989-07-31 | 1991-12-31 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5021440A (en) * | 1989-07-31 | 1991-06-04 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5019572A (en) * | 1990-02-07 | 1991-05-28 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US4968713A (en) * | 1989-07-31 | 1990-11-06 | Merck & Co., Inc. | Certain imidazole compounds as transglutaminase inhibitors |
| RU2662308C1 (ru) * | 2017-12-25 | 2018-07-25 | Феркат Адельзянович Халиуллин | Средство для лечения и профилактики тромбоза |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1238350A (fr) * | 1959-06-30 | 1960-08-12 | Inst Nat Rech Chimique | Procédé d'obtention d'amines sulfurées |
| US3895010A (en) * | 1972-12-13 | 1975-07-15 | Dow Chemical Co | 1-(Arylthio)methanesulfonamides |
| JPS5829784B2 (ja) * | 1975-08-22 | 1983-06-24 | 萬有製薬株式会社 | オメガ − （ アリ−ルスルホンアミド ）− アルキルアミンノ セイホウ |
| US4098889A (en) * | 1977-09-01 | 1978-07-04 | The Dow Chemical Company | Antithrombotic 2-(aminoalkylthio)-N,N'-p-phenylenebissulfonamides |
-
1978
- 1978-08-01 EP EP78300227A patent/EP0000826A1/en not_active Withdrawn
- 1978-08-01 DK DK340178A patent/DK340178A/da unknown
- 1978-08-01 ZA ZA00784348A patent/ZA784348B/xx unknown
- 1978-08-02 ES ES472290A patent/ES472290A1/es not_active Expired
- 1978-08-02 AU AU38577/78A patent/AU3857778A/en active Pending
- 1978-08-02 FI FI782383A patent/FI782383A/fi not_active Application Discontinuation
- 1978-08-02 IT IT26405/78A patent/IT1099585B/it active
- 1978-08-02 NO NO782650A patent/NO782650L/no unknown
- 1978-08-02 NZ NZ188038A patent/NZ188038A/xx unknown
- 1978-08-03 JP JP9500178A patent/JPS5444635A/ja active Pending
- 1978-08-03 US US05/930,614 patent/US4218476A/en not_active Expired - Lifetime
- 1978-08-03 PT PT68382A patent/PT68382A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT68382A (en) | 1978-09-01 |
| ZA784348B (en) | 1979-07-25 |
| NZ188038A (en) | 1981-02-11 |
| DK340178A (da) | 1979-02-06 |
| FI782383A (fi) | 1979-02-06 |
| EP0000826A1 (en) | 1979-02-21 |
| AU3857778A (en) | 1980-02-07 |
| ES472290A1 (es) | 1979-02-16 |
| US4218476A (en) | 1980-08-19 |
| JPS5444635A (en) | 1979-04-09 |
| IT7826405A0 (it) | 1978-08-02 |
| IT1099585B (it) | 1985-09-18 |
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