DD222025A5 - Verfahren zur herstellung neuer flavene oder thioflavene - Google Patents

Verfahren zur herstellung neuer flavene oder thioflavene Download PDF

Info

Publication number: DD222025A5
Authority: DD; German Democratic Republic
Prior art keywords: substituted; formula; phenyl; unsubstituted; formyl
Prior art date: 1983-08-31

Application number

DD84266736A

Other languages

German (de)

English (en)

Inventor

Christian G Rimbault

Philippe M Narbel

Original Assignee

Zyma Sa

Priority date (The priority date 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 date listed.)

1983-08-31

Filing date

1984-08-29

Publication date

1985-05-08

1984-08-29 Application filed by Zyma Sa filed Critical Zyma Sa

1985-05-08 Publication of DD222025A5 publication Critical patent/DD222025A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 5
YQXGMDHETWBHLV-UHFFFAOYSA-N 2-phenyl-4h-thiochromene Chemical compound S1C2=CC=CC=C2CC=C1C1=CC=CC=C1 YQXGMDHETWBHLV-UHFFFAOYSA-N 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 54
230000008569 process Effects 0.000 claims abstract description 13
-1 2-acetoxy-2-phenylethyl Chemical group 0.000 claims description 313
150000001875 compounds Chemical class 0.000 claims description 302
125000000217 alkyl group Chemical group 0.000 claims description 151
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 114
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 113
229910052736 halogen Inorganic materials 0.000 claims description 111
150000002367 halogens Chemical class 0.000 claims description 108
125000003282 alkyl amino group Chemical group 0.000 claims description 98
125000003545 alkoxy group Chemical group 0.000 claims description 84
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
125000004414 alkyl thio group Chemical group 0.000 claims description 55
150000003839 salts Chemical class 0.000 claims description 54
125000002252 acyl group Chemical group 0.000 claims description 50
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 49
229910052717 sulfur Inorganic materials 0.000 claims description 49
239000011593 sulfur Chemical group 0.000 claims description 49
125000001424 substituent group Chemical group 0.000 claims description 47
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 46
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 39
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 37
125000004093 cyano group Chemical group *C#N 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 34
239000004215 Carbon black (E152) Substances 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 33
229930195733 hydrocarbon Natural products 0.000 claims description 32
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 30
125000003396 thiol group Chemical class [H]S* 0.000 claims description 30
229910052760 oxygen Inorganic materials 0.000 claims description 29
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
239000001301 oxygen Substances 0.000 claims description 28
125000003342 alkenyl group Chemical group 0.000 claims description 27
229910052796 boron Inorganic materials 0.000 claims description 27
229910052727 yttrium Inorganic materials 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
125000005237 alkyleneamino group Chemical group 0.000 claims description 22
125000004442 acylamino group Chemical group 0.000 claims description 21
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 21
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 20
125000004423 acyloxy group Chemical group 0.000 claims description 18
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 17
125000001841 imino group Chemical group [H]N=* 0.000 claims description 16
150000001721 carbon Chemical group 0.000 claims description 15
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 15
150000004820 halides Chemical class 0.000 claims description 13
125000001931 aliphatic group Chemical group 0.000 claims description 12
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
125000005605 benzo group Chemical group 0.000 claims description 12
125000004468 heterocyclylthio group Chemical group 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
125000005236 alkanoylamino group Chemical group 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
239000011707 mineral Substances 0.000 claims description 9
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 8
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
125000001302 tertiary amino group Chemical group 0.000 claims description 8
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
125000005210 alkyl ammonium group Chemical group 0.000 claims description 7
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
241000534944 Thia Species 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000003302 alkenyloxy group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
150000002902 organometallic compounds Chemical class 0.000 claims description 5
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 4
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
LRMJVYUTQDYWMS-UHFFFAOYSA-N 4-ethoxy-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O1C2=CC=CC=C2C(OCC)=C(C=O)C1C1=CC=CC=C1 LRMJVYUTQDYWMS-UHFFFAOYSA-N 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims 2
241000251730 Chondrichthyes Species 0.000 claims 1
125000006319 alkynyl amino group Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000007924 injection Substances 0.000 abstract description 5
238000002347 injection Methods 0.000 abstract description 5
239000012530 fluid Substances 0.000 abstract description 2
238000012545 processing Methods 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 41
150000003254 radicals Chemical class 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000007787 solid Substances 0.000 description 18
239000007858 starting material Substances 0.000 description 18
239000013078 crystal Substances 0.000 description 17
150000007513 acids Chemical class 0.000 description 16
238000011282 treatment Methods 0.000 description 16
AIOQBOPOGHAITF-UHFFFAOYSA-N 4-chloro-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O1C2=CC=CC=C2C(Cl)=C(C=O)C1C1=CC=CC=C1 AIOQBOPOGHAITF-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
238000007792 addition Methods 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
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 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
239000002904 solvent Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
229910021529 ammonia Inorganic materials 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
239000011734 sodium Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
235000010755 mineral Nutrition 0.000 description 8
210000003097 mucus Anatomy 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
229910004298 SiO 2 Inorganic materials 0.000 description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
150000008044 alkali metal hydroxides Chemical class 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
230000009467 reduction Effects 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
150000003335 secondary amines Chemical class 0.000 description 7
238000003756 stirring Methods 0.000 description 7
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
108010010803 Gelatin Proteins 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000008273 gelatin Substances 0.000 description 6
229920000159 gelatin Polymers 0.000 description 6
235000019322 gelatine Nutrition 0.000 description 6
235000011852 gelatine desserts Nutrition 0.000 description 6
206010019692 hepatic necrosis Diseases 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000012360 testing method Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
125000000304 alkynyl group Chemical group 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000003814 drug Substances 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
125000002950 monocyclic group Chemical group 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 5
MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 4
HJSTVTHRVHYLCP-UHFFFAOYSA-N 3-chloro-2-phenyl-2h-chromene-4-carbaldehyde Chemical compound ClC1=C(C=O)C2=CC=CC=C2OC1C1=CC=CC=C1 HJSTVTHRVHYLCP-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical class O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
239000004593 Epoxy Substances 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
239000000427 antigen Substances 0.000 description 4
102000036639 antigens Human genes 0.000 description 4
108091007433 antigens Proteins 0.000 description 4
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
230000008034 disappearance Effects 0.000 description 4
239000008298 dragée Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000284 extract Substances 0.000 description 4
208000006454 hepatitis Diseases 0.000 description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
239000008101 lactose Substances 0.000 description 4
231100000149 liver necrosis Toxicity 0.000 description 4
210000002540 macrophage Anatomy 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000002734 organomagnesium group Chemical group 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229920001592 potato starch Chemical class 0.000 description 4
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230000007866 hepatic necrosis Effects 0.000 description 1
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150000004677 hydrates Chemical class 0.000 description 1
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XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
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239000003456 ion exchange resin Substances 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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238000002955 isolation Methods 0.000 description 1
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WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
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CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
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GSUMTMZOJQAWLW-UHFFFAOYSA-N n-[(3-chloro-2-phenyl-2h-chromen-4-yl)methylidene]hydroxylamine Chemical compound O1C2=CC=CC=C2C(C=NO)=C(Cl)C1C1=CC=CC=C1 GSUMTMZOJQAWLW-UHFFFAOYSA-N 0.000 description 1
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239000007922 nasal spray Substances 0.000 description 1
229940097496 nasal spray Drugs 0.000 description 1
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ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004971 nitroalkyl group Chemical group 0.000 description 1
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QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
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125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
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239000008363 phosphate buffer Substances 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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229910052697 platinum Inorganic materials 0.000 description 1
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235000015277 pork Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
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125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
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238000000197 pyrolysis Methods 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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239000010948 rhodium Substances 0.000 description 1
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150000003333 secondary alcohols Chemical class 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
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230000004622 sleep time Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
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QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
150000003512 tertiary amines Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
150000003582 thiophosphoric acids Chemical class 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical group FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000001173 tumoral effect Effects 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
229910001935 vanadium oxide Inorganic materials 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Gastroenterology & Hepatology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Paints Or Removers (AREA)
Saccharide Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyrane Compounds (AREA)
Seasonings (AREA)
Fats And Perfumes (AREA)

DD84266736A 1983-08-31 1984-08-29 Verfahren zur herstellung neuer flavene oder thioflavene DD222025A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB838323293A GB8323293D0 (en)	1983-08-31	1983-08-31	Substituted flavene and thioflavene derivatives

Publications (1)

Publication Number	Publication Date
DD222025A5 true DD222025A5 (de)	1985-05-08

Family

ID=10548081

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84266736A DD222025A5 (de)	1983-08-31	1984-08-29	Verfahren zur herstellung neuer flavene oder thioflavene

Country Status (19)

Country	Link
US (1)	US4665202A (fr)
EP (1)	EP0140830B1 (fr)
JP (1)	JPS60149581A (fr)
AT (1)	ATE45878T1 (fr)
AU (1)	AU577308B2 (fr)
CA (1)	CA1247615A (fr)
DD (1)	DD222025A5 (fr)
DE (1)	DE3479564D1 (fr)
DK (1)	DK416184A (fr)
ES (1)	ES8802308A1 (fr)
FI (1)	FI83780C (fr)
GB (2)	GB8323293D0 (fr)
GR (1)	GR80260B (fr)
HU (1)	HUT36819A (fr)
IL (1)	IL72776A (fr)
NO (1)	NO843455L (fr)
NZ (1)	NZ209395A (fr)
PT (1)	PT79146B (fr)
ZA (1)	ZA846786B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8323292D0 (en) *	1983-08-31	1983-10-05	Zyma Sa	Flavene and thioflavene derivatives
JPH0758454B2 (ja)	1987-07-14	1995-06-21	キヤノン株式会社	座標入力装置
GB8805628D0 (en) *	1988-03-09	1988-04-07	Erba Farmitalia	Hypolipidaemic imidazol-2-yl-derivatives of bicyclic compounds & process for their preparation
US5763470A (en) *	1995-06-07	1998-06-09	Sugen Inc.	Benzopyran compounds and methods for their use
CN1234029A (zh) *	1996-08-27	1999-11-03	盐野义制药株式会社	色烯－3－羚酸衍生物
US6034256A (en) *	1997-04-21	2000-03-07	G.D. Searle & Co.	Substituted benzopyran derivatives for the treatment of inflammation
US6077850A (en) *	1997-04-21	2000-06-20	G.D. Searle & Co.	Substituted benzopyran analogs for the treatment of inflammation
WO1999042459A1 (fr) *	1998-02-18	1999-08-26	Shionogi & Co., Ltd.	Procede de production d'un derive de chromene optiquement actif
AU2001261006A1 (en) *	2000-03-28	2001-10-08	Chugai Seiyaku Kabushiki Kaisha	Benzopyranes useful as tnf alpha inhibitors
DK1578741T3 (da) *	2002-12-23	2011-09-26	4Sc Ag	Aromatiske forbindelser som anti-inflammatoriske, immunmodulatoriske og anti-proliferative midler

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE357755C (de) *	1920-03-27	1922-08-31	Chemische Fabriken Vorm Weiler	Verfahren zur Herstellung von Kondensationsprodukten aus ª‡íñª‰-ungesaettigten Ketonen und Phenolen
DE1493976C3 (de) *	1964-01-18	1973-09-13	Merck Patent Gmbh, 6100 Darmstadt	Substituierte Flavandenvate sowie Verfahren zu ihrer Herstellung
US3567605A (en) *	1966-03-30	1971-03-02	Ralph S Becker	Photochemical process
US3796727A (en) *	1972-01-31	1974-03-12	Eastman Kodak Co	Synthesis of novel benzopyran compounds
JPS5651470A (en) *	1979-09-13	1981-05-09	Wellcome Found	Flavan derivative
DE3300004A1 (de) *	1983-01-03	1984-07-12	Bayer Ag, 5090 Leverkusen	Substituierte 4-aminomethylenchromane bzw. -chromene, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
HU194214B (en) *	1983-02-15	1988-01-28	Alkaloida Vegyeszeti Gyar	Process for producing 7-alkoxy-2h-chromene derivatives and insecticide and nematocide compositions containing them as active components
US4557783A (en) *	1983-12-05	1985-12-10	Cincinnati Milacron Inc.	Composite tape laying machine and method

1983
- 1983-08-31 GB GB838323293A patent/GB8323293D0/en active Pending
1984
- 1984-08-24 US US06/644,006 patent/US4665202A/en not_active Expired - Fee Related
- 1984-08-27 DE DE8484810424T patent/DE3479564D1/de not_active Expired
- 1984-08-27 AT AT84810424T patent/ATE45878T1/de active
- 1984-08-27 EP EP84810424A patent/EP0140830B1/fr not_active Expired
- 1984-08-27 FI FI843364A patent/FI83780C/fi not_active IP Right Cessation
- 1984-08-27 IL IL72776A patent/IL72776A/xx unknown
- 1984-08-28 PT PT79146A patent/PT79146B/pt not_active IP Right Cessation
- 1984-08-29 GB GB08421778A patent/GB2145720B/en not_active Expired
- 1984-08-29 CA CA000462008A patent/CA1247615A/fr not_active Expired
- 1984-08-29 DD DD84266736A patent/DD222025A5/de not_active IP Right Cessation
- 1984-08-30 NO NO843455A patent/NO843455L/no unknown
- 1984-08-30 AU AU32572/84A patent/AU577308B2/en not_active Ceased
- 1984-08-30 DK DK416184A patent/DK416184A/da not_active Application Discontinuation
- 1984-08-30 HU HU843262A patent/HUT36819A/hu unknown
- 1984-08-30 ZA ZA846786A patent/ZA846786B/xx unknown
- 1984-08-30 NZ NZ209395A patent/NZ209395A/en unknown
- 1984-08-30 GR GR80260A patent/GR80260B/el unknown
- 1984-08-31 ES ES535590A patent/ES8802308A1/es not_active Expired
- 1984-08-31 JP JP59180892A patent/JPS60149581A/ja active Pending

Also Published As

Publication number	Publication date
HUT36819A (en)	1985-10-28
EP0140830B1 (fr)	1989-08-30
AU3257284A (en)	1986-09-11
GB2145720B (en)	1987-02-04
FI843364A7 (fi)	1985-03-01
NO843455L (no)	1985-03-01
PT79146A (en)	1984-09-01
ES535590A0 (es)	1988-05-01
EP0140830A2 (fr)	1985-05-08
AU577308B2 (en)	1988-09-22
CA1247615A (fr)	1988-12-28
FI83780C (fi)	1991-08-26
NZ209395A (en)	1987-11-27
FI83780B (fi)	1991-05-15
GB2145720A (en)	1985-04-03
ES8802308A1 (es)	1988-05-01
IL72776A0 (en)	1984-11-30
US4665202A (en)	1987-05-12
GR80260B (en)	1985-01-02
DE3479564D1 (en)	1989-10-05
GB8421778D0 (en)	1984-10-03
FI843364A0 (fi)	1984-08-27
DK416184D0 (da)	1984-08-30
IL72776A (en)	1991-01-31
PT79146B (en)	1986-11-14
JPS60149581A (ja)	1985-08-07
GB8323293D0 (en)	1983-10-05
DK416184A (da)	1985-03-01
ATE45878T1 (de)	1989-09-15
EP0140830A3 (en)	1986-01-08
ZA846786B (en)	1985-04-24

Legal Events

Date	Code	Title	Description
1996-05-09	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2100242C2 (de)	1984-07-19	1-Methyl-2-(3a,4,5,6,7,7a-hexahydro-1,2-benzisoxazol-3-yl)-5-nitroimidazol, Verfahren zu dessen Herstellung und dieses enthaltende Veterinärarzneimittel
DE2228012C3 (de)	1980-01-17	Phthalidester der 6- [D(-)- a Aminophenylacetamido] -penicillansäure und Verfahren zu seiner Herstellung
DE1445154B2 (de)	1973-07-05	1,4-dihydro-1,8-naphthyridinderivate und ein verfahren zu ihrer herstellung
DE2516025A1 (de)	1975-11-06	Neue pyridinderivate, ihre herstellung und verwendung
CH627754A5 (de)	1982-01-29	Verfahren zur herstellung von neuen chinazolonderivaten.
DD222025A5 (de)	1985-05-08	Verfahren zur herstellung neuer flavene oder thioflavene
EP0019081A1 (fr)	1980-11-26	Dérivés de flavone, leur préparation, ces flavones et flavones connues en soi en tant qu'agents antiviraux et compositions pharmaceutiques les contenant
DE4102103A1 (de)	1992-08-20	Substituierte benzoxazepine und benzthiazepine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
EP0051819A2 (fr)	1982-05-19	Dérivés tétra substitués de benzène, leur préparation et préparations pharmaceutiques les contenant
DD210687A5 (de)	1984-06-20	Verfahren zur herstellung von (+)-cyanidan-3-ol-derivaten
DE69030044T2 (de)	1997-10-09	Tetrazolessigsäurederivate mit Aldosereduktase inhibierender Wirkung
EP0697405B1 (fr)	2002-08-14	Dérivés de quinoléines substituées, procédé pour leur préparation et leur utilisation
DD210908A5 (de)	1984-06-27	Verfahren zur herstellung von ketenthioacetaten
EP0021000B1 (fr)	1984-02-22	Acétophénones substituées, leur préparation et compositions pharmaceutiques les contenant
AT371462B (de)	1983-06-27	Verfahren zur herstellung neuer benzopyranderivate und ihrer salze
DE2952652A1 (de)	1980-07-24	1,2-dihydro-2-oxonikotinsaeurederivate und diese enthaltende arzneimittel
DD249019A5 (de)	1987-08-26	Verfahren zur herstellung von tricyclischen verbindungen
CH618176A5 (fr)	1980-07-15
DD234008A5 (de)	1986-03-19	Flavene and thioflavene derivates, processes for their manufacture, pharmaceutical preparationsthat contain such compounds, and the use of the latter
CH634839A5 (de)	1983-02-28	Pyranochromonderivate und ihre verwendung in arzneimitteln zur behandlung von allergien.
DD295846A5 (de)	1991-11-14	Verfahren zur herstellung weiterer neuer alkanophenone
DE68905361T2 (de)	1993-09-30	Trienische Derivate mit chromenischer Struktur, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen.
DE2819215C2 (fr)	1990-12-13
EP0196330B1 (fr)	1992-07-01	Utilisation des derives de la pyrrothine
DE69103985T2 (de)	1995-03-30	N-Alkylthiazolidinderivate.