DD251339A5 - Verfahren zur herstellung von neuen phenolderivaten - Google Patents

Verfahren zur herstellung von neuen phenolderivaten Download PDF

Info

Publication number: DD251339A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; group; compound; same meaning; hydrogen
Prior art date: 1985-05-24

Application number

DD86290483A

Other languages

German (de)

English (en)

Inventor

Oswald K Zimmer

Werner P Vollenberg

Gerriet K H Loschen

Werner Winter

Erwin O Kiesewetter

Ulrich G P Seipp

Original Assignee

��@��k��

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.)

1985-05-24

Filing date

1986-05-22

Publication date

1987-11-11

1986-05-22 Application filed by ��@��k�� filed Critical ��@��k��

1987-11-11 Publication of DD251339A5 publication Critical patent/DD251339A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 59
238000002360 preparation method Methods 0.000 title claims abstract description 21
230000008569 process Effects 0.000 title claims abstract description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 191
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 34
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 20
230000015572 biosynthetic process Effects 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
150000002431 hydrogen Chemical class 0.000 claims abstract description 16
239000003054 catalyst Substances 0.000 claims abstract description 11
229910052763 palladium Inorganic materials 0.000 claims abstract description 10
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
229910052751 metal Chemical class 0.000 claims abstract 2
239000002184 metal Chemical class 0.000 claims abstract 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 65
-1 hydroxy, acetyloxy Chemical group 0.000 claims description 40
238000006243 chemical reaction Methods 0.000 claims description 31
125000006239 protecting group Chemical group 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
230000003197 catalytic effect Effects 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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 claims description 9
150000007513 acids Chemical class 0.000 claims description 9
238000003776 cleavage reaction Methods 0.000 claims description 9
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 9
230000007017 scission Effects 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
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 7
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
229910052744 lithium Inorganic materials 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
230000009471 action Effects 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 5
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 5
229910052740 iodine Chemical group 0.000 claims description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Chemical group 0.000 claims description 4
230000008030 elimination Effects 0.000 claims description 4
238000003379 elimination reaction Methods 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
150000001879 copper Chemical class 0.000 claims description 2
229910052731 fluorine Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 11
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
239000000010 aprotic solvent Substances 0.000 claims 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
150000003335 secondary amines Chemical class 0.000 claims 1
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 abstract description 8
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 abstract description 8
150000001299 aldehydes Chemical class 0.000 abstract description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
150000002989 phenols Chemical class 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 5
150000002617 leukotrienes Chemical class 0.000 abstract description 5
125000000217 alkyl group Chemical group 0.000 abstract description 2
238000007239 Wittig reaction Methods 0.000 abstract 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
125000001931 aliphatic group Chemical group 0.000 abstract 1
125000002534 ethynyl group Chemical class [H]C#C* 0.000 abstract 1
VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 282
238000005160 1H NMR spectroscopy Methods 0.000 description 82
239000000243 solution Substances 0.000 description 74
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
239000003208 petroleum Substances 0.000 description 64
239000000047 product Substances 0.000 description 61
238000004440 column chromatography Methods 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
229910052757 nitrogen Inorganic materials 0.000 description 20
238000003756 stirring Methods 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000013078 crystal Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000012043 crude product Substances 0.000 description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 12
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 6
239000000284 extract Substances 0.000 description 6
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
150000003180 prostaglandins Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
206010030113 Oedema Diseases 0.000 description 5
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 5
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
SXYFAZGVNNYGJQ-UHFFFAOYSA-M chloromethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCl)C1=CC=CC=C1 SXYFAZGVNNYGJQ-UHFFFAOYSA-M 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
230000003266 anti-allergic effect Effects 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000009472 formulation Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 4
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
FSZNIQKHBJCCCR-UHFFFAOYSA-N undeca-1,9-diyne Chemical compound C#CCCCCCCC#CC FSZNIQKHBJCCCR-UHFFFAOYSA-N 0.000 description 4
SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 3
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 3
KGIJOOYOSFUGPC-XRXZHELTSA-N 5-hydroxyeicosatetraenoic acid Natural products CCCCCC=CCC=CCC=C\C=C\C(O)CCCC(O)=O KGIJOOYOSFUGPC-XRXZHELTSA-N 0.000 description 3
229910004664 Cerium(III) chloride Inorganic materials 0.000 description 3
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000002804 anti-anaphylactic effect Effects 0.000 description 3
230000001088 anti-asthma Effects 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
230000001741 anti-phlogistic effect Effects 0.000 description 3
239000000924 antiasthmatic agent Substances 0.000 description 3
229940114079 arachidonic acid Drugs 0.000 description 3
235000021342 arachidonic acid Nutrition 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
210000000265 leukocyte Anatomy 0.000 description 3
WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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150000004820 halides Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000036512 infertility Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
YJWVMUJXPCIJLQ-UHFFFAOYSA-N methyl 2-acetyloxy-5-(11-acetyloxyundeca-1,9-diynyl)benzoate Chemical compound COC(=O)C1=CC(C#CCCCCCCC#CCOC(C)=O)=CC=C1OC(C)=O YJWVMUJXPCIJLQ-UHFFFAOYSA-N 0.000 description 1
GCYFHUYWTAALLP-UHFFFAOYSA-N methyl 2-hydroxy-5-(11-hydroxyundeca-1,9-diynyl)-3-methoxybenzoate Chemical compound COC(=O)C1=CC(C#CCCCCCCC#CCO)=CC(OC)=C1O GCYFHUYWTAALLP-UHFFFAOYSA-N 0.000 description 1
KBZQGYACLDOFLJ-UHFFFAOYSA-N methyl 2-hydroxy-5-(11-hydroxyundeca-1,9-diynyl)benzoate Chemical compound COC(=O)C1=CC(C#CCCCCCCC#CCO)=CC=C1O KBZQGYACLDOFLJ-UHFFFAOYSA-N 0.000 description 1
210000001589 microsome Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
235000011007 phosphoric acid Nutrition 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
229920000570 polyether Polymers 0.000 description 1
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
PDFGPBXCEASWLG-UHFFFAOYSA-N propyl 2-hydroxy-5-iodobenzoate Chemical compound CCCOC(=O)C1=CC(I)=CC=C1O PDFGPBXCEASWLG-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
JFFXPDGGTDBAEZ-UHFFFAOYSA-N tert-butyl-(4-ethynyl-2,6-dimethoxyphenoxy)-dimethylsilane Chemical group COC1=CC(C#C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C JFFXPDGGTDBAEZ-UHFFFAOYSA-N 0.000 description 1
GSJFIIAHOSYGLK-UHFFFAOYSA-N tert-butyl-(4-ethynyl-2,6-dimethoxyphenoxy)-diphenylsilane Chemical group COC1=CC(C#C)=CC(OC)=C1O[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 GSJFIIAHOSYGLK-UHFFFAOYSA-N 0.000 description 1
LRDKUINTJXCHMB-UHFFFAOYSA-N tert-butyl-[4-(2-chloroethenyl)-2,6-dimethoxyphenoxy]-dimethylsilane Chemical compound COC1=CC(C=CCl)=CC(OC)=C1O[Si](C)(C)C(C)(C)C LRDKUINTJXCHMB-UHFFFAOYSA-N 0.000 description 1
FCIMVIXBNIWHMA-UHFFFAOYSA-N tert-butyl-diphenyl-prop-2-ynoxysilane Chemical compound C=1C=CC=CC=1[Si](OCC#C)(C(C)(C)C)C1=CC=CC=C1 FCIMVIXBNIWHMA-UHFFFAOYSA-N 0.000 description 1
AVCOOKDJFUGKMG-UHFFFAOYSA-N tert-butyl-oct-1-yn-3-yloxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OC(CCCCC)C#C)C1=CC=CC=C1 AVCOOKDJFUGKMG-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds

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Pulmonology (AREA)
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Molecular Biology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Signal Processing For Digital Recording And Reproducing (AREA)
Fixed Capacitors And Capacitor Manufacturing Machines (AREA)
Emergency Protection Circuit Devices (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD86290483A 1985-05-24 1986-05-22 Verfahren zur herstellung von neuen phenolderivaten DD251339A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853518655 DE3518655A1 (de)	1985-05-24	1985-05-24	Neue phenolderivate, diese enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel

Publications (1)

Publication Number	Publication Date
DD251339A5 true DD251339A5 (de)	1987-11-11

Family

ID=6271506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86290483A DD251339A5 (de)	1985-05-24	1986-05-22	Verfahren zur herstellung von neuen phenolderivaten

Country Status (17)

Country	Link
US (2)	US4760087A (es)
EP (1)	EP0202529B1 (es)
JP (1)	JPH0796507B2 (es)
KR (1)	KR930001324B1 (es)
AT (1)	ATE48591T1 (es)
CA (1)	CA1272723A (es)
DD (1)	DD251339A5 (es)
DE (2)	DE3518655A1 (es)
DK (1)	DK240086A (es)
ES (1)	ES8704868A1 (es)
FI (1)	FI88708C (es)
GR (1)	GR860777B (es)
HU (1)	HU196048B (es)
IL (1)	IL78317A0 (es)
PT (1)	PT82521B (es)
SU (1)	SU1591800A3 (es)
ZA (1)	ZA862432B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1230859B (it) *	1989-06-05	1991-11-08	Corvi Camillo Spa	2 alchinilfenoli sostituiti ad azione anti infiammatoria, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono.
DE4120698A1 (de) *	1991-06-22	1992-12-24	Gruenenthal Gmbh	Substituierte phenoxyalkanole und deren ester, diese verbindungen enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel
US5981591A (en) *	1992-12-04	1999-11-09	Mayor Pharmaceutical Laboratories, Inc.	Sprayable analgesic composition and method of use
US6767925B1 (en)	1996-10-31	2004-07-27	Joseph A. Deihl	Sprayable analgesic composition and method of use
DE19845372A1 (de) *	1998-10-02	2000-04-20	Gruenenthal Gmbh	Verwendung von Katecholderivaten als Proteinaseninhibitoren

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3033668A (en) *	1958-03-27	1962-05-08	Dow Chemical Co	Method for inhibiting nitrification of ammonium nitrogen in soil
US4393075A (en) *	1980-04-14	1983-07-12	Takeda Chemical Industries, Ltd.	Quinone compounds and their use in suppressing the production of SRS-A in mammals
JPS56150014A (en) *	1980-04-21	1981-11-20	Takeda Chem Ind Ltd	Antiallergic agent
EP0056172B1 (en) *	1981-01-09	1985-04-03	FISONS plc	Phenoxy- and thiophenoxy compounds, methods for their preparation and pharmaceutical formulations containing them
US4432906A (en) *	1981-09-14	1984-02-21	Hoffmann-La Roche Inc.	Inhibitors of SRS-synthesis
IE54269B1 (en) *	1981-12-30	1989-08-02	Ici America Inc	Pharmaceutically active phenylcarboxylic acid derivatives
US4497827A (en) *	1982-08-30	1985-02-05	Syntex (U.S.A.) Inc.	Arachidonic acid analogues as anti-inflammatory and anti-allergic agents
EP0123543B1 (en) *	1983-04-21	1988-02-03	Merck Frosst Canada Inc.	Leukotriene antagonists, their production and use and compositions containing them
JPS59204167A (ja) *	1983-05-02	1984-11-19	Takeda Chem Ind Ltd	ヒドロキノン誘導体およびその製法
US4499295A (en) *	1983-05-09	1985-02-12	G. D. Searle & Co.	Protease inhibitors
US4618627A (en) *	1983-05-13	1986-10-21	Yamanouchi Pharmaceutical Co., Ltd.	Catechol derivatives and pharmaceutical compositions thereof for inhibiting anaphylaxis (SRS-A)
US5105017A (en) *	1983-07-18	1992-04-14	Eli Lilly And Company	Leukotriene antagonist intermediates
IL72385A (en) *	1983-07-18	1988-03-31	Lilly Co Eli	Leukotriene antagonistic tetrasubstituted benzene derivatives,their preparation and pharmaceutical preparations containing them
US4590304A (en) *	1984-03-21	1986-05-20	The United States Of America As Represented By The Secretary Of The Air Force	Protected ethynylated phenols
US4733002A (en) *	1984-05-23	1988-03-22	Green Cross Corporation	Lipoxygenase inhibitor
US4564476A (en) *	1984-10-29	1986-01-14	Mcneilab, Inc.	Aryl fatty acid leukotriene synthesis inhibitors
GB8430072D0 (en) *	1984-11-28	1985-01-09	Lilly Industries Ltd	Pharmaceutical compounds

1985
- 1985-05-24 DE DE19853518655 patent/DE3518655A1/de not_active Withdrawn
1986
- 1986-03-26 GR GR860777A patent/GR860777B/el unknown
- 1986-03-28 IL IL78317A patent/IL78317A0/xx not_active IP Right Cessation
- 1986-04-02 CA CA000505690A patent/CA1272723A/en not_active Expired - Fee Related
- 1986-04-02 ZA ZA862432A patent/ZA862432B/xx unknown
- 1986-04-30 ES ES554611A patent/ES8704868A1/es not_active Expired
- 1986-05-05 AT AT86106126T patent/ATE48591T1/de not_active IP Right Cessation
- 1986-05-05 DE DE8686106126T patent/DE3667461D1/de not_active Expired - Fee Related
- 1986-05-05 EP EP86106126A patent/EP0202529B1/de not_active Expired
- 1986-05-06 PT PT82521A patent/PT82521B/pt not_active IP Right Cessation
- 1986-05-07 SU SU864027431A patent/SU1591800A3/ru active
- 1986-05-13 US US06/862,649 patent/US4760087A/en not_active Expired - Lifetime
- 1986-05-21 HU HU862148A patent/HU196048B/hu not_active IP Right Cessation
- 1986-05-22 DD DD86290483A patent/DD251339A5/de not_active IP Right Cessation
- 1986-05-22 DK DK240086A patent/DK240086A/da not_active Application Discontinuation
- 1986-05-23 JP JP61117656A patent/JPH0796507B2/ja not_active Expired - Fee Related
- 1986-05-23 FI FI862184A patent/FI88708C/fi not_active IP Right Cessation
- 1986-05-24 KR KR1019860004098A patent/KR930001324B1/ko not_active IP Right Cessation
1988
- 1988-07-14 US US07/218,981 patent/US4959391A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0202529B1 (de)	1989-12-13
PT82521B (pt)	1988-03-03
IL78317A0 (en)	1986-07-31
ES554611A0 (es)	1987-04-16
HU196048B (en)	1988-09-28
FI88708B (fi)	1993-03-15
AU587456B2 (en)	1989-08-17
CA1272723A (en)	1990-08-14
EP0202529A3 (en)	1988-08-03
ATE48591T1 (de)	1989-12-15
HUT43805A (en)	1987-12-28
JPS61271238A (ja)	1986-12-01
GR860777B (en)	1986-07-18
US4760087A (en)	1988-07-26
AU5758186A (en)	1986-11-27
KR930001324B1 (ko)	1993-02-26
ES8704868A1 (es)	1987-04-16
DK240086D0 (da)	1986-05-22
JPH0796507B2 (ja)	1995-10-18
DE3518655A1 (de)	1986-11-27
FI862184A0 (fi)	1986-05-23
DE3667461D1 (de)	1990-01-18
ZA862432B (en)	1986-11-26
SU1591800A3 (ru)	1990-09-07
KR860008963A (ko)	1986-12-19
FI88708C (fi)	1993-06-28
US4959391A (en)	1990-09-25
DK240086A (da)	1986-11-25
FI862184A (fi)	1986-11-25
EP0202529A2 (de)	1986-11-26
PT82521A (de)	1986-06-01

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2001-01-04	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP1655280A1 (de)	2006-05-10	Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften
DE3219244A1 (de)	1982-12-09	Sulfonatderivate, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel
EP0641759B1 (de)	1998-12-09	Verwendung aromatischer Carbonsäurederivate zur Herstellung von pharmazeutischen Präparaten
EP0084667B1 (de)	1985-09-18	Phenylethylen-Derivate, ihre Herstellung und Verwendung als Arzneimittel
EP0176035B1 (de)	1990-06-06	1-substituierte Tetralinderivate, ihre Herstellung und Verwendung
DE2242239A1 (de)	1973-03-22	Neue 2-descarboxy-2- eckige klammer auf tetrazol-5-yl eckige klammer zu prostaglandine, verfahren zu ihrer herstellung sowie zwischenprodukte
EP0099538B1 (de)	1991-09-11	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2719244A1 (de)	1977-11-17	Neue derivate des 11-desoxy-prostaglandin-f tief 2 , verfahren zu deren herstellung und pharmazeutische zusammensetzungen
DD251339A5 (de)	1987-11-11	Verfahren zur herstellung von neuen phenolderivaten
EP0009777B1 (de)	1982-05-05	Retinsäure- und 7,8-Dehydro-retinsäure-N-(carboxy)-phenyl-amide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
DE3202118A1 (de)	1983-07-28	Substituierte vinylbenzoesaeure-derivate, ihre herstellung und diese enthaltende pharmazeutische zubereitungen
EP0009776B1 (de)	1982-07-28	N-Monohydroxypropylamide, N-Dihydroxypropylamide und deren Acetonoide der all-E- und 13-Z-Retinsäure, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
DE3853126T2 (de)	1995-06-14	Derivate der fluorierten Arachidonsäure.
DE2945781A1 (de)	1980-06-12	Prostacyclinzwischenprodukte und protacyclinanaloge
DE3515278A1 (de)	1986-10-30	Neue benzoesaeurederivate, diese enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel
DD244132A5 (de)	1987-03-25	Verfahren zur herstellung von /4.2.0/ bicyclooctanderivaten
DE2458911A1 (de)	1975-06-26	11,12-secoprostaglandine und verfahren zu ihrer herstellung
EP0080718B1 (de)	1986-05-14	Inter-m-Phenylen-PGI2-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate
EP0001255B1 (de)	1981-09-30	Neue fluorhaltige Prostaglandinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
IE58359B1 (en)	1993-09-08	New phenol derivatives, pharmaceutical compositions containing these compounds and processes for the preparation of these compounds and compositions
CH638195A5 (de)	1983-09-15	Prostacyclinanaloge.
AT392071B (de)	1991-01-25	Neue prostacycline
EP0413692B1 (de)	1993-10-20	Verwendung von hexatrienderivaten zur herstellung von mitteln gegen akne, psoriasis und lichtschäden der haut
DE2354085C3 (de)	1977-11-24	11,12 -Secoprostaglandine, Arzneimittel, welche diese enthalten, und Verfahren zu ihrer Herstellung
EP0080061A1 (de)	1983-06-01	Neue cis-Bicyclo(3.3.0)octanderivate, diese enthaltende Arzneimittel und Verfahren zur Herstellung dieser Verbindungen und Arzneimittel