KR830009072A - 카복실산 유도체의 제조방법 - Google Patents
카복실산 유도체의 제조방법 Download PDFInfo
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- KR830009072A KR830009072A KR1019820000091A KR820000091A KR830009072A KR 830009072 A KR830009072 A KR 830009072A KR 1019820000091 A KR1019820000091 A KR 1019820000091A KR 820000091 A KR820000091 A KR 820000091A KR 830009072 A KR830009072 A KR 830009072A
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- 238000000034 method Methods 0.000 title claims 30
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 33
- 238000006243 chemical reaction Methods 0.000 claims 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 19
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 150000001412 amines Chemical class 0.000 claims 7
- 239000002585 base Substances 0.000 claims 7
- -1 cyano, hydroxy Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 238000009835 boiling Methods 0.000 claims 4
- 239000012954 diazonium Substances 0.000 claims 4
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 150000001989 diazonium salts Chemical class 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 150000007522 mineralic acids Chemical class 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- 239000012190 activator Substances 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000001569 carbon dioxide Substances 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000007530 organic bases Chemical group 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000005695 dehalogenation reaction Methods 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 239000002274 desiccant Substances 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229910052751 metal Chemical class 0.000 claims 1
- 239000002184 metal Chemical class 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Abstract
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Description
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Claims (32)
- a) 일반식(XI)의 카복실산 또는 반응혼합물에서 임의 제조된 그의 반응유도체를 일반식(XII)의 아민 또는 반응혼합물에서 임의 형성된 일반식(XII)의 N-활성화된 아민(이때는 일반식(XI)의 카복실산을 사용하며 일반식(XII)의 N-활성화된 아민중의 Z가 카복시기를 나타내지 않는다)과 반응시키거나, b) X가 CH-기이고 m이 0인 일반식(I)의 화합물을 제조하기 위해서 일반식(XIII)의 화합물을 일반식(XIV)의 아민과 반응시키거나, c) Z가 카복시기인 일반식(I)의 화합물을 제조하기 위해서 일반식(XV)화합물을 산화시키거나 d) Z가 카복시기인 일반식(I)의 화합물을 제조하기 위해서 일반식(XVI) 화합물을 가수분해 시키거나, e) X가 CH-기이고 m이 0인 일반식(I) 화합물을 제조하기 위해서 일반식(XVII)화합물이나 그의 알카리염을 일반식(XVIII)화합물과 반응시키거나, f) X가 CH-기이고 Z가 카복시기인 일반식(I)화합물을 제조하기 위해서 일반식(XIX)화합물을 루이스산 존재하에서 옥살릴 할로게-나이드나 포스겐으로 아실화시키거나, g) X가 CH-기이고 Z가 카복시기인 일반식(I)화합물을 제조하기 위해서 일반식(XX)의 화합물을 반응혼합물에서 임의 제조된 하이포할로게나이트와 반응시키거나 경우에 따라서 수득된 Z가 카복시기인 일반식(I)화합물을 계속하여 에스테르화하여 Z가 에스테르화된 카복시그룹을 나타내는 상응하는 일반식(I)화합물을 그의 부가염 특히 무기산 또는 유기산 및 염기(Z가 카복시 그룹인 경우에는)와의 생리학적으로 무독한 염으로 전환시킴을 특징으로 하여 일반식(I)의 화합물을 제조하는 방법.상기식에서m은 0 또는 1의 정수이고;n은 1 또는 2의 정수이고;R은 수소원자 또는 탄소원자수 1내지 3의 알킬기이며,R1은 수소, 불소, 염소, 브롬 또는 요오드원자, 각각 탄소원자수 1 내지 4의 알킬 또는 알콕시기, 시아노, 히드록시 또는 트리플루오로메틸기이거나, 탄소수 1 내지 3의 알킬기나 불소, 염소 또는 브롬원자로 임의 치환된 페닐기이며;R2및 R3는 이들이 부착된 질소원자와 함께 피페리디노, 3,5-디메틸-피페리디노, 옥타하이드로-1H-아조니노, 데카하이드로-아제시노, 1,3-디하이드로-이소-인돌로, 헥사하이드로-이소인돌로 또는 옥타하이드로-이소인돌로기, 탄소원자 5 내지 10의 알킬기로 치환된 피페리디노기, 바이시클로알칸환에서 탄소원자수 7 내지 12의 아자바이시클로알킬기로 각각 탄소원자수 1 내지 3을 가진 하나 또는 2 이상의 알킬기로 치환될 수 있거나, 할로겐 원자나 탄소원자 1 내지 3의 알콕시기 또는 아미노기로 치환된 1,3-디하이드로-이소인돌로기, m이 정수 1이면 또한 피롤리디노, 헥사메틸렌이미노 또는 헵타메틸렌이미노기를 나타내며;X는 CH-기 또는 질소원자를 나타내며;R8은 수소원자, 탄소원자 1 내지 3의 알킬기나 아릴기를 나타내며;Z는 임의 에스테르화된 카복시기 뿐만아니라 비대칭성 탄소원자가 있으면 그의 광학적 활성 대칭체 및 그의 부가염(특히 그의 무기 또는 유기산과 Z가 카복시기이면 또한 염기와의 생리학적으로 무독한 염)을 나타내며;E는 할로겐원자와 같이 교환 가능한 라디칼을 나타내며;G는 산화에 의해 카복시기로 변형할 수 있는 기를 나타내며;Q는 가수분해에 의해 카복시기로 변형할 수 있는 기를 나타내며;Y는 할로겐원자나 설포닐옥시기와 같은 친해성 유출기를 나타낸다.
- a) W가 카복시기인 일반식(Ia)화합물을 제조하기 위해 일반식(II)화합물을 가수분해시키거나, b) R5가 아미노기를 나타내는 일반식(Ia)화합물을 제조하기 위해서 일반식(III)의 니트로 화합물을 환원시키거나, c) R5가 히드록시기, 시아노기, 수소, 불소, 염소 또는 브롬원자인 일반식(Ia)화합물을 제조하기 위해서 일반식(IV)화합물을 아질산염과 반응시키고 계속해서 수득한 디아조늄염을 황산의 존재하에서나 구리의 존재하에서 또는 상응하는 구리-(I)-염 존재하에서 가열시키거나, d) R5가 수소원자를 나타내는 일반식(Ia)화합물을 제조하기 위해서 일반식(V)화합물을 탈할로겐화시키거나, e) W가 카복시기를 나타내는 일반식(Ia)화합물을 제조하기 위해서 일반식(VI) 화합물을 이산화 탄소와 반응시키거나, f) X가 질소원자를 나타내는 일반식(Ia)화합물을 제조하기 위해서 일반식(VII)화합물을 일반식(VIII)의 아민과 반응시키거나, g) R5가 탄소원자수 1 내지 4의 알콕시기를 나타내는 일반식(Ia)화합물을 제조하기 위해서 일반식(IX) 화합물을 일반식(X)화합물과 반응시키고 경우에 따라 계속해서 가수분해시키거나, 경우에 따라 수득한 W가 에스테르화된 카복시기를 나타내는 일반식(Ia)화합물을 가수분해하여 W가 카복시기인 일반식(Ia) 화합물로 전환시키거나 및/또는 수득한 일반식(Ia)화합물을 그의 무기 또는 유기산 및 염기(W가 카복시 그룹인 경우)와의 부가염으로 전환시킴을 특징으로 하여 일반식(Ia)의 2-아미노-카복실산 유도체 뿐만 아니라 비대칭성 탄소원자가 있으면 그의 광학적 활성 대칭체 및 그의 부가염을 제조하는 방법.상기식에서m은 0 또는 1의 정수이고;W는 임의로 에스테르화된 카복시기를 나타내며;X는 질소원자 또는 CH-기를 나타내면;R은 수소원자 또는 탄소원자수 1 내지 3의 알킬기이며;R5는 수소 또는 할로겐원자, 아미노, 시아노, 히드록시 카복시 또는 아세트아미노기, 각각 탄소원자수 1 내지 4의 알킬 또는 알콕시기를 나타내며;R6와 R7은 이들이 부착된 질소원자와 함께 탄소원자 5 내지 10을 가진 알킬기로 치환된 피페리디노기, 바이시클로알칸환에서 탄소원자수 7 내지 12를 가진 아자바이시클로알킬기로 탄소원자수 1 내지 3을 가진 하나 또는 그 이상의 알킬기로 치환될 수 있거나, 옥타하이드로-1H-아조니노, 1,3-디하이드로-이소인돌로, 헥사하이드로-이소인돌로 또는 옥타하이드로-이소인돌로기, 또는 할로겐원자나 탄소원자수 1내지 3의 알콕시기 또는 아미노기로 치환된 1,3-디하이드로-이소인돌로기를 나타내며;R8은 수소원자, 탄소원자 1 내지 3의 알킬기나 아릴기를 나타내며;A는 가수분해에 의해 카복시기로 변환될 수 있는 기를 나타내며;Hal은 할로겐원자를 나타내며;Me는 알카리금속원자 또는 알카리 토금속 할로게나이드 라디칼을 나타내며;B는 교환될 수 있는 라디칼을 나타내며;R5'는 탄소수 1 내지 4의 알킬기를 나타내며;D는 친핵성 유출기를 나타내거나, 라디칼 R5'의 인접된 수소와 함께 디아조기를 나타낸다.
- 제1항 또는 제2항에 있어서, 반응을 용매중에서 실시함을 특징으로 하는 방법.
- 제1항 (a) 또는 제3항에 있어서, 반응을 산활성화제 또는 탈수제의 존재하에서 무기 또는 3급 유기열기의 존재는 임의로 하여 실시함을 특징으로 하는 방법.
- 제1항 a) 또는 제3항에 있어서, 반응을 아민 활성화제의 존재하에서 무기 또는 3급 유기염기의 존재는 임의로하여 실시함을 특징으로 하는 방법.
- 제1항 a) 또는 제3항에 있어서, 용액시키는 동안 생성된 물을 공비 증류에 의해서나 건조제를 가하여 제거시킴을 특징으로 하는 방법.
- 제1항 a)나 제3항에 내지 제6항중의 어느 하나에 있어서, 반응을 -25 내지 250℃에서, 바람직하게 -10℃내지 사용된 용매의 비등온도에서 실시함을 특징으로 하는 방법.
- 제1항 b) 또는 제3항에 있어서, 반응을 과량의 일반식(XIV)의 아민 존재하에서 시행함을 특징으로 하는 방법.
- 제1항 b)나 제3항 내지 제8항중의 어느 하나에 있어서, 반응을 무기 또는 3급 유기 염기 존재하, 동과같은 반응 촉진제 존재하 및/또는 밀폐 용기중에서 시행함을 특징으로 하는 방법.
- 제1항 b), 제8항 또는 제9항에 있어서, 반응을 20 내지 150℃온도, 바람직하게는 반응혼합물의 비등온도, 예를들면 100℃에서 시행함을 특징으로 하는 방법.
- 제1항 c) 또는 제3항에 있어서, 반응을 0 내지 100℃ 바람직하게는 20 내지 50℃에서 시행함을 특징으로 하는 방법.
- 제1항 d) 또는 제3항에 있어서, 가수분해를 산 또는 염기 존재하에 시행함을 특징으로 하는 방법.
- 제1항 d) 또는 제3항 또는 제12항에 있어서, 반응을 반응혼합물의 비등온도에서 시행함을 특징으로 하는 방법.
- 제1항 e) 또는 제3항에 있어서, 반응을 나트륨 하이드리드 또는 칼륨-3급 부틸레이트와 같은 염기 존재하에 시행함을 특징으로 하는 방법.
- 제1항 e) 또는 제3항 또는 제14항에 있어서, 반응을 20 내지 180℃ 바람직하게는 50 내지 150℃ 온도에서 시행함을 특징으로 하는 방법.
- 제1항 f) 또는 제3항에 있어서, 루이스 산으로서 알루미늄 클로라이드를 사용함을 특징으로 하는 방법.
- 제1항 f) 또는 제3항 또는 제16항에 있어서, 반응을 0 내지 80℃, 바람직하게는 20 내지 60℃ 온도에서 시행함을 특징으로 하는 방법.
- 제1항 g) 또는 제3항에 있어서, 반응을 0 내지 80℃, 바람직하게는 25 내지 50℃ 온도에서 시행함을 특징으로 하는 방법.
- 제2항 또는 제3항에 있어서, 가수분해를 산 또는 염기 존재하에 시행함을 특징으로 하는 방법.
- 제19항에 있어서, 반응을 -10내지 120℃ 바람직하게는 실온내지 반응혼합물의 비등온도에서 시행함을 특징으로 하는 방법.
- 제2항 b) 또는 제3항에 있어서, 환원을 0 내지 50℃ 온도에서 시행함을 특징으로 하는 방법.
- 제2항 b), 제3항 또는 21항에 있어서, 환원반응을 촉매적으로 활성화된 수소, 라니-니켈 존재하의 하이드라진, 발생기 수소 또는 금속 염과 함께 시행함을 특징으로 하는 방법.
- 제2항 c) 또는 제3항에 있어서, 디아조늄 열을 저온, 예를들면 -10 내지 5℃ 온도에서 제조함을 특징으로 하는 방법.
- 제2항 c), 제3항 또는 제23항에 있어서, 제조된 디아조늄 염 예를들면 플루오로보레이트, 하이드로설페이트를 황산 존재하에 또는 하이드로클로라이드를 동존재하에 또는 동(I)-클로라이드/염산, 동(I)-브로마이드/브롬산과 같은 상응하는 동-(I)-열의 존재하에 가열하여 상응하는 화합물로 전환시킴을 특징으로 하는 방법.
- 제24항에 있어서, 디아조늄염을 15 내지 90℃ 온도까지 가열시킴을 특징으로 하는 방법.
- 제2항 d) 또는 제3항에 있어서, 탈할로겐화 반응을 촉매적으로 활성화시킨 수소를 사용하여 시행함을 특징으로 하는 방법.
- 제2항 d), 3항 또는 26항에 있어서, 반응을 0 내지 75℃ 온도 바람직하게는 실온에서 1 내지 5 바아의 수소압에서 시행함을 특징으로 하는 방법.
- 제2항에 있어서, 일반식(VI)의 화합물을 고체 이산화탄소에 가함을 특징으로 하는 방법.
- 제2항 f) 또는 제3항에 있어서, 반응을 20 내지 150℃ 적절하게는 80 내지 100℃ 온도에서 시행함을 특징으로 하는 방법.
- 제2항 f), 제3항 또는 제26항에 있어서, 반응을 동과 같은 반응촉진제 존재하에 시행함을 특징으로 하는 방법.
- 제2항 g) 또는 제3항에 있어서, 알킬화를 염기 존재하에 시행함을 특징으로 하는 방법.
- 제2항 g), 제3항에 있어서, 반응을 0 내지 100℃ 바람직하게는 15 내지 70℃에서 시행함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3100535A DE3100535A1 (de) | 1981-01-10 | 1981-01-10 | "neue carbonsaeure-derivate, ihre herstellung und ihre verwendung als arzneimittel" |
| DE3100535 | 1981-01-10 |
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| Publication Number | Publication Date |
|---|---|
| KR830009072A true KR830009072A (ko) | 1983-12-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019820000091A KR830009072A (ko) | 1981-01-10 | 1982-01-09 | 카복실산 유도체의 제조방법 |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0056144A1 (ko) |
| JP (1) | JPS57140766A (ko) |
| KR (1) | KR830009072A (ko) |
| AU (1) | AU7929082A (ko) |
| CS (1) | CS236668B2 (ko) |
| DD (1) | DD202021A5 (ko) |
| DE (1) | DE3100535A1 (ko) |
| DK (1) | DK536281A (ko) |
| ES (4) | ES508586A0 (ko) |
| FI (1) | FI820060L (ko) |
| GB (2) | GB2091729A (ko) |
| GR (1) | GR75135B (ko) |
| HU (1) | HU187561B (ko) |
| IL (1) | IL64732A0 (ko) |
| NO (1) | NO820046L (ko) |
| PH (1) | PH20430A (ko) |
| PL (2) | PL238405A1 (ko) |
| PT (1) | PT74262A (ko) |
| ZA (1) | ZA82149B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3139970A1 (de) * | 1981-10-08 | 1983-04-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| DE3211934A1 (de) * | 1982-03-31 | 1983-10-13 | Hoechst Ag, 6230 Frankfurt | Salicylsaeurederivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| DE3320583A1 (de) * | 1983-06-08 | 1984-12-13 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue galenische zubereitungsformen von oralen antidiabetika und verfahren zu ihrer herstellung |
| DE3320582A1 (de) * | 1983-06-08 | 1984-12-13 | Dr. Karl Thomae Gmbh, 7950 Biberach | Gliquidonhaltige zubereitungsformen und verfahren zu ihrer herstellung |
| US5312924A (en) | 1983-12-30 | 1994-05-17 | Dr. Karl Thomae Gmbh | Phenylacetic acid benzylamides |
| DE3347565A1 (de) * | 1983-12-30 | 1985-07-11 | Thomae Gmbh Dr K | Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US5216167A (en) * | 1983-12-30 | 1993-06-01 | Dr. Karl Thomae Gmbh | Phenylacetic acid benzylamides |
| JPS61165372A (ja) * | 1985-01-17 | 1986-07-26 | Daicel Chem Ind Ltd | ５−ハロピリジン−３−カルボキサミド化合物 |
| JPH0710846B2 (ja) * | 1985-01-18 | 1995-02-08 | ダイセル化学工業株式会社 | ４−置換オキシ−３−ピリジンカルボキサミド化合物 |
| EP0716656A1 (en) * | 1993-09-03 | 1996-06-19 | Smithkline Beecham Plc | Amide derivatives as 5ht1d receptor antagonists |
| US20050261278A1 (en) | 2004-05-21 | 2005-11-24 | Weiner David M | Selective serotonin receptor inverse agonists as therapeutics for disease |
| CN101137758B (zh) | 2004-11-03 | 2012-10-10 | 意力速分子诊断股份有限公司 | 均相分析物检测 |
| ES2376578T3 (es) | 2004-11-03 | 2012-03-15 | Iris Molecular Diagnostics, Inc. | Microburbujas para separación por afinidad. |
| KR20070112775A (ko) * | 2005-01-10 | 2007-11-27 | 아카디아 파마슈티칼스 인코포레이티드 | 선택적인 안드로겐 수용체 조절자로서의 아미노페닐 유도체 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163788A (en) * | 1968-03-27 | 1979-08-07 | Ciba-Geigy Corporation | Tertiary aminoacids |
| DE2500157C2 (de) * | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
| DE2655144A1 (de) * | 1976-12-06 | 1978-06-08 | Basf Ag | Substituierte nicotinsaeureamide |
| DE3016650A1 (de) * | 1979-07-13 | 1981-11-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 2-amino-benzoesaeure-derivate, deren herstellung und deren verwendung als arzneimittel oder zwischenprodukte |
| DE3016651A1 (de) * | 1980-04-30 | 1981-11-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue carbonsaeureamide, deren herstellung und diese sie enthaltende arzneimittel |
| EP0023569B1 (de) * | 1979-07-13 | 1983-06-22 | Dr. Karl Thomae GmbH | Carbonsäure-Derivate, deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2928352A1 (de) * | 1979-07-13 | 1981-01-15 | Thomae Gmbh Dr K | Neue aminobenzoesaeureamide, ihre herstellung und ihre verwendung als arzneimittel |
| DE2949259A1 (de) * | 1979-07-13 | 1981-06-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue aminobenzoesaeureamide, ihre herstellung und ihre verwendung als arzneimittel |
-
1981
- 1981-01-10 DE DE3100535A patent/DE3100535A1/de not_active Withdrawn
- 1981-12-03 DK DK536281A patent/DK536281A/da not_active Application Discontinuation
- 1981-12-23 EP EP81110731A patent/EP0056144A1/de not_active Ceased
-
1982
- 1982-01-04 GR GR66965A patent/GR75135B/el unknown
- 1982-01-07 DD DD82236614A patent/DD202021A5/de unknown
- 1982-01-08 IL IL64732A patent/IL64732A0/xx unknown
- 1982-01-08 PL PL23840582A patent/PL238405A1/xx unknown
- 1982-01-08 NO NO820046A patent/NO820046L/no unknown
- 1982-01-08 CS CS82178A patent/CS236668B2/cs unknown
- 1982-01-08 PH PH26760A patent/PH20430A/en unknown
- 1982-01-08 HU HU8258A patent/HU187561B/hu unknown
- 1982-01-08 GB GB8200489A patent/GB2091729A/en not_active Withdrawn
- 1982-01-08 AU AU79290/82A patent/AU7929082A/en not_active Abandoned
- 1982-01-08 PL PL23466282A patent/PL234662A1/xx unknown
- 1982-01-08 ES ES508586A patent/ES508586A0/es active Granted
- 1982-01-08 FI FI820060A patent/FI820060L/fi not_active Application Discontinuation
- 1982-01-08 PT PT74262A patent/PT74262A/pt unknown
- 1982-01-09 KR KR1019820000091A patent/KR830009072A/ko unknown
- 1982-01-11 ZA ZA82149A patent/ZA82149B/xx unknown
- 1982-01-11 JP JP57001885A patent/JPS57140766A/ja active Pending
- 1982-07-09 ES ES513844A patent/ES8306137A1/es not_active Expired
- 1982-07-09 ES ES513846A patent/ES513846A0/es active Granted
- 1982-07-09 ES ES513845A patent/ES513845A0/es active Granted
-
1984
- 1984-09-04 GB GB848422314A patent/GB8422314D0/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO820046L (no) | 1982-07-12 |
| ES8305345A1 (es) | 1983-04-01 |
| FI820060L (fi) | 1982-07-11 |
| PH20430A (en) | 1987-01-05 |
| ES8305718A1 (es) | 1983-04-16 |
| ZA82149B (en) | 1983-09-28 |
| CS236668B2 (en) | 1985-05-15 |
| ES513846A0 (es) | 1983-04-16 |
| AU7929082A (en) | 1982-07-22 |
| PL234662A1 (en) | 1983-01-31 |
| ES8304145A1 (es) | 1983-02-16 |
| PT74262A (pt) | 1982-02-01 |
| ES508586A0 (es) | 1983-02-16 |
| JPS57140766A (en) | 1982-08-31 |
| GB2091729A (en) | 1982-08-04 |
| ES513844A0 (es) | 1983-05-01 |
| PL238405A1 (en) | 1983-05-23 |
| ES513845A0 (es) | 1983-04-01 |
| DK536281A (da) | 1982-07-11 |
| GR75135B (ko) | 1984-07-13 |
| DE3100535A1 (de) | 1982-08-12 |
| GB8422314D0 (en) | 1984-10-10 |
| DD202021A5 (de) | 1983-08-24 |
| ES8306137A1 (es) | 1983-05-01 |
| IL64732A0 (en) | 1982-03-31 |
| HU187561B (en) | 1986-01-28 |
| EP0056144A1 (de) | 1982-07-21 |
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