JPH0524147B2 - - Google Patents
Info
- Publication number
- JPH0524147B2 JPH0524147B2 JP63323884A JP32388488A JPH0524147B2 JP H0524147 B2 JPH0524147 B2 JP H0524147B2 JP 63323884 A JP63323884 A JP 63323884A JP 32388488 A JP32388488 A JP 32388488A JP H0524147 B2 JPH0524147 B2 JP H0524147B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkyl
- hydrogen atom
- general formula
- salt
- 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 - Lifetime
Links
- -1 halogenophenyl group Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- 239000002904 solvent Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 238000001816 cooling Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000010531 catalytic reduction reaction Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WPGPRLVPWACBHW-UHFFFAOYSA-N (4-methoxy-4-oxobutyl)azanium;chloride Chemical compound Cl.COC(=O)CCCN WPGPRLVPWACBHW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 description 2
- SWQHKHCSCVCGMS-UHFFFAOYSA-N 4-chloro-n-(2,3-dihydro-1h-inden-2-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1CC2=CC=CC=C2C1 SWQHKHCSCVCGMS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000005189 Embolism Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002468 indanes Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FKHGAFIKZYQKRR-UHFFFAOYSA-N 2-[(4-methoxy-4-oxobutyl)amino]-2-oxoacetic acid Chemical compound COC(=O)CCCNC(=O)C(O)=O FKHGAFIKZYQKRR-UHFFFAOYSA-N 0.000 description 1
- IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical compound SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- 206010003225 Arteriospasm coronary Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- 208000003890 Coronary Vasospasm Diseases 0.000 description 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 206010037437 Pulmonary thrombosis Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
- YOZSRQSUXWJLEU-UHFFFAOYSA-N benzyl 2-chloro-2-oxoacetate Chemical compound ClC(=O)C(=O)OCC1=CC=CC=C1 YOZSRQSUXWJLEU-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 201000011634 coronary artery vasospasm Diseases 0.000 description 1
- 208000002528 coronary thrombosis Diseases 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 1
- WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- XPGRZDJXVKFLHQ-UHFFFAOYSA-N hydron;methyl 3-aminopropanoate;chloride Chemical compound Cl.COC(=O)CCN XPGRZDJXVKFLHQ-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 208000001286 intracranial vasospasm Diseases 0.000 description 1
- 229910052742 iron Inorganic materials 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
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- FVMGEDMQPDXFDC-UHFFFAOYSA-N methyl 4-[[2-[2-[(4-chlorophenyl)sulfonylamino]-2,3-dihydro-1h-inden-5-yl]acetyl]amino]butanoate Chemical compound C1C2=CC(CC(=O)NCCCC(=O)OC)=CC=C2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 FVMGEDMQPDXFDC-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- AQZTVRSXYOQPOA-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)formamide Chemical compound C1=CC=C2CC(NC=O)CC2=C1 AQZTVRSXYOQPOA-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 239000003769 thromboxane A2 receptor blocking agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63323884A JPH02169563A (ja) | 1988-12-22 | 1988-12-22 | インダン誘導体の製法及びその合成中間体 |
| CN89109011A CN1025563C (zh) | 1988-12-22 | 1989-11-30 | 制备茚满衍生物的方法 |
| GR890100822A GR1000458B (el) | 1988-12-22 | 1989-12-13 | Μεθοδος για την παρασκευη παραγωγων του ινδανιου. |
| ES8904304A ES2019199A6 (es) | 1988-12-22 | 1989-12-20 | Un procedimiento para preparar un derivado de indano. |
| FI896116A FI896116A0 (fi) | 1988-12-22 | 1989-12-20 | Foerfarande foer framstaellning av indanderivat. |
| HU896730A HU206196B (en) | 1988-12-22 | 1989-12-21 | Process for producing indane derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63323884A JPH02169563A (ja) | 1988-12-22 | 1988-12-22 | インダン誘導体の製法及びその合成中間体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02169563A JPH02169563A (ja) | 1990-06-29 |
| JPH0524147B2 true JPH0524147B2 (da) | 1993-04-06 |
Family
ID=18159677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63323884A Granted JPH02169563A (ja) | 1988-12-22 | 1988-12-22 | インダン誘導体の製法及びその合成中間体 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH02169563A (da) |
| CN (1) | CN1025563C (da) |
| ES (1) | ES2019199A6 (da) |
| FI (1) | FI896116A0 (da) |
| GR (1) | GR1000458B (da) |
| HU (1) | HU206196B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2321268A2 (en) * | 2008-08-15 | 2011-05-18 | F. Hoffmann-La Roche AG | Bi-aryl aminotetralines |
| CN103539709B (zh) * | 2013-03-22 | 2015-11-25 | 湖北生物医药产业技术研究院有限公司 | N-(-1-氢-茚-1-基)磺酰胺类化合物及其制备方法和用途 |
| CN115872907B (zh) * | 2021-09-29 | 2024-01-30 | 中国石油化工股份有限公司 | 一种磺酸盐稠油降粘剂及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623944A1 (de) * | 1986-07-16 | 1988-02-11 | Thomae Gmbh Dr K | Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| IL88314A (en) * | 1987-11-18 | 1994-05-30 | Tanabe Seiyaku Co | History of sulfonylamino indane, their preparation and pharmaceutical preparations containing them |
-
1988
- 1988-12-22 JP JP63323884A patent/JPH02169563A/ja active Granted
-
1989
- 1989-11-30 CN CN89109011A patent/CN1025563C/zh not_active Expired - Fee Related
- 1989-12-13 GR GR890100822A patent/GR1000458B/el unknown
- 1989-12-20 ES ES8904304A patent/ES2019199A6/es not_active Expired - Lifetime
- 1989-12-20 FI FI896116A patent/FI896116A0/fi not_active Application Discontinuation
- 1989-12-21 HU HU896730A patent/HU206196B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR1000458B (el) | 1992-07-30 |
| CN1025563C (zh) | 1994-08-03 |
| HUT52753A (en) | 1990-08-28 |
| CN1043703A (zh) | 1990-07-11 |
| FI896116A0 (fi) | 1989-12-20 |
| HU206196B (en) | 1992-09-28 |
| ES2019199A6 (es) | 1991-06-01 |
| HU896730D0 (en) | 1990-02-28 |
| JPH02169563A (ja) | 1990-06-29 |
| GR890100822A (en) | 1991-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0442820B1 (fr) | Nouveaux dérivés de benzimidazole et d'azabenzimidazole, antagonistes des récepteurs au thromboxane; leurs procédés de préparation, intermédiaires de synthèse, compositions les contenant | |
| FR2838438A1 (fr) | Derives de diphenylpyridine,leur preparation, les compositions pharmaceutiques en contenant | |
| JP2007517056A5 (da) | ||
| JP2010501587A (ja) | ４−置換フェノキシフェニル酢酸誘導体 | |
| CA2590681A1 (fr) | Derives de n- [ (4 , 5-diphenyl-3-alkyl-2-thienyl) methyl] amine (amide, sulfonamide, carbamate et uree) comme antagonists des recepteurs cb1 des cannabinoides | |
| HU201003B (en) | Process for producing indan derivatives and pharmaceutical compositions compirising same | |
| Harvill et al. | Haloalkyltetrazole and aminoalkyltetrazole derivatives | |
| JPH0524147B2 (da) | ||
| JP2006512302A (ja) | ＡＣＡＴ阻害活性を有するα−フェニルアセトアニリド誘導体およびその治療的適用 | |
| EP0858459B1 (fr) | Nouveaux derives de pyrazoles acides, leur procede de preparation, leur application a titre de medicaments, leur nouvelle utilisation et les compositions pharmaceutiques les renfermant | |
| JP5305593B2 (ja) | 高化学的ｒ−５−（２−（２−エトキシフェノキシエチルアミノ）プロピル）−２−メトキシベンゼンスルホンアミド塩酸塩の調製 | |
| SU786892A3 (ru) | Способ получени сульфонилбензимидазолов | |
| JP2945957B2 (ja) | 含フッ素一級アミンの製造法 | |
| CA2170097C (fr) | Nouveaux composes du thiophene, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| KR20060085631A (ko) | 아자바이사이클로[3.1.0]헥산 화합물의 제조방법 | |
| US5998666A (en) | Phenoxyethylamine derivatives, method of preparation, application as medicine and pharmaceutical compositions containing same | |
| JPH03284657A (ja) | 光学活性ノルボルナン系アミン誘導体の製造方法 | |
| BE858864A (fr) | Nouveaux esters d'acides phenyl- et pyridine-3-carboxylique et procede permettant leur preparation | |
| JP3799580B2 (ja) | Ｎ−置換−ｎ−スルホニルアミド類の製造方法 | |
| CA1183137A (fr) | [(piperidyl-4)-2 alkyl-1 ethyl]-3 indoles et leur utilisation comme medicaments | |
| JPH03190854A (ja) | インダン誘導体の製法及びその合成中間体 | |
| JPH0557262B2 (da) | ||
| JPH08253459A (ja) | １，２，３−トリアゾール類の改良された経済的な製造方法 | |
| JPH0784381B2 (ja) | トロンボキサンａ▲下２▼拮抗薬 | |
| JPH0524148B2 (da) |