DE2658938A1 - Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel - Google Patents
Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittelInfo
- Publication number
- DE2658938A1 DE2658938A1 DE19762658938 DE2658938A DE2658938A1 DE 2658938 A1 DE2658938 A1 DE 2658938A1 DE 19762658938 DE19762658938 DE 19762658938 DE 2658938 A DE2658938 A DE 2658938A DE 2658938 A1 DE2658938 A1 DE 2658938A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- group
- compounds
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229940126601 medicinal product Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 32
- -1 amino, carboxyl Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 150000002923 oximes Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 239000003513 alkali Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000001631 hypertensive effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000466 oxiranyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000002443 hydroxylamines Chemical group 0.000 claims description 2
- 238000003780 insertion Methods 0.000 claims description 2
- 230000037431 insertion Effects 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 229960002715 nicotine Drugs 0.000 claims description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 230000001077 hypotensive effect Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 238000009530 blood pressure measurement Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 3
- 229960001289 prazosin Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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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
- C07D213/24—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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
-
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (32)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762658938 DE2658938A1 (de) | 1976-12-24 | 1976-12-24 | Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| NL7714054A NL7714054A (nl) | 1976-12-24 | 1977-12-19 | Basisch gesubstitueerde o-propyloximen, werkwij- ze voor het bereiden daarvan en werkwijze voor het bereiden van een geneesmiddel met bloeddruk- verlagende werking. |
| ES465204A ES465204A1 (es) | 1976-12-24 | 1977-12-19 | Procedimiento para la produccion de 0-propiloximas sustitui-das con restos basicos. |
| ZA00777586A ZA777586B (en) | 1976-12-24 | 1977-12-21 | Novel o-propyloximes |
| AU31811/77A AU512353B2 (en) | 1976-12-24 | 1977-12-21 | Phenyl piperidine and phenyl piperazine derivatives |
| GB53220/77A GB1543517A (en) | 1976-12-24 | 1977-12-21 | O-propyl-oximes |
| GR55042A GR70042B (cg-RX-API-DMAC7.html) | 1976-12-24 | 1977-12-22 | |
| SE7714685A SE7714685L (sv) | 1976-12-24 | 1977-12-22 | Forfarande for framstellning av nya basiskt substituerade o-propyloximer samt deras anvendning sasom lekemedel |
| IE2605/77A IE46226B1 (en) | 1976-12-24 | 1977-12-22 | Novel o-propyloximes |
| AT924777A AT360544B (de) | 1976-12-24 | 1977-12-22 | Verfahren zur herstellung von neuen piperazin- - und piperidinderivaten und ihren salzen |
| DK575277A DK575277A (da) | 1976-12-24 | 1977-12-22 | Fremgangsmaade til fremstilling af basisk substituerede 0-propyloximer |
| IL53674A IL53674A (en) | 1976-12-24 | 1977-12-22 | 3-(4-phenylpiperazinyl or 4-phenylpiperidyl) o-propyloximes,their preparation and pharmaceutical compositions comprising them |
| PT67444A PT67444B (en) | 1976-12-24 | 1977-12-22 | A process for the preparation of novel basically substituted o-propyloximes and their use as pharmaceuticals |
| FI773903A FI773903A7 (fi) | 1976-12-24 | 1977-12-22 | Nya basiskt substituerade 0-propyloximer foerfarande foer deras framstaellning och deras anvaendning som laekemedel |
| NO774456A NO774456L (no) | 1976-12-24 | 1977-12-23 | Fremgangsmaate til fremstilling av nye basisk substituerte o-propyloksimer og deres anvendelse som legemiddel |
| HU77HO2037A HU177453B (en) | 1976-12-24 | 1977-12-23 | Process for preparing new basic substituted o-propyloximes and pharmaceutical preparations containing thereof |
| BE183831A BE862303A (fr) | 1976-12-24 | 1977-12-23 | Nouvelles 0-propyloximes substituees basiquement, leur procede de preparation et leur emploi comme medicaments |
| LU78770A LU78770A1 (cg-RX-API-DMAC7.html) | 1976-12-24 | 1977-12-23 | |
| IT31206/77A IT1089233B (it) | 1976-12-24 | 1977-12-23 | O-propilossime sostituite con sostituenti basici,procedimento per la loro preparazione e loro impiego come prodotti medicinali |
| FR7739023A FR2375225A1 (fr) | 1976-12-24 | 1977-12-23 | Nouvelles o-propyloximes substituees basiquement, leur procede de preparation et leur emploi comme medicaments |
| CA293,826A CA1105933A (en) | 1976-12-24 | 1977-12-23 | O-propyloximes |
| JP15547977A JPS5379875A (en) | 1976-12-24 | 1977-12-23 | Basically substituted novel propyloxime process for preparing same and medical application thereof |
| PL1977203359A PL110753B1 (en) | 1976-12-24 | 1977-12-24 | Method of producing new basically substituted o-propyloximes |
| PL1977214671A PL111792B1 (en) | 1976-12-24 | 1977-12-24 | Method of manufacture of novel,base substituted o-propyloximes |
| PL1977214670A PL112153B1 (en) | 1976-12-24 | 1977-12-24 | Method of manufacture of novel base substituted o-propyloximes |
| ES469456A ES469456A1 (es) | 1976-12-24 | 1978-05-04 | Procedimiento para la produccion de o-propiloximas sustitui-das con restos basicos. |
| ES469455A ES469455A1 (es) | 1976-12-24 | 1978-05-04 | Procedimiento para la produccion de o-propiloximas sustitui-das con restos basicos. |
| JP2205679A JPS54141784A (en) | 1976-12-24 | 1979-02-28 | Novel basically substituted oopropyloxime* its manufacture and its use as medicine |
| AT48180A AT361000B (de) | 1976-12-24 | 1980-01-30 | Verfahren zur herstellung von neuen piperazin- - und piperidinderivaten und ihren salzen |
| US06/150,705 US4328227A (en) | 1976-12-24 | 1980-05-19 | Novel O-propyloximes |
| JP7845480A JPS5695166A (en) | 1976-12-24 | 1980-06-12 | Novel basically substituted oopropyloxime* its manufacture and its use as medicine |
| JP7845580A JPS5677275A (en) | 1976-12-24 | 1980-06-12 | Novel basically substituted oopropyloxime* its manufacture and its use as medicine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762658938 DE2658938A1 (de) | 1976-12-24 | 1976-12-24 | Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2658938A1 true DE2658938A1 (de) | 1978-07-06 |
Family
ID=5996701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762658938 Withdrawn DE2658938A1 (de) | 1976-12-24 | 1976-12-24 | Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4328227A (cg-RX-API-DMAC7.html) |
| JP (4) | JPS5379875A (cg-RX-API-DMAC7.html) |
| AT (1) | AT360544B (cg-RX-API-DMAC7.html) |
| AU (1) | AU512353B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE862303A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1105933A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2658938A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK575277A (cg-RX-API-DMAC7.html) |
| ES (3) | ES465204A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI773903A7 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2375225A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1543517A (cg-RX-API-DMAC7.html) |
| GR (1) | GR70042B (cg-RX-API-DMAC7.html) |
| HU (1) | HU177453B (cg-RX-API-DMAC7.html) |
| IE (1) | IE46226B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL53674A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1089233B (cg-RX-API-DMAC7.html) |
| LU (1) | LU78770A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL7714054A (cg-RX-API-DMAC7.html) |
| NO (1) | NO774456L (cg-RX-API-DMAC7.html) |
| PL (3) | PL112153B1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT67444B (cg-RX-API-DMAC7.html) |
| SE (1) | SE7714685L (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA777586B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0617012A1 (de) * | 1993-03-02 | 1994-09-28 | BASF Aktiengesellschaft | Beta-Hydroxyoximether und bei Raumtemperatur mit beta-Hydroxyoximethern vernetzbare Dispersionen oder Lösungen |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3704604A1 (de) * | 1987-02-13 | 1988-08-25 | Mack Chem Pharm | Oximether von 2,6-dioxabicyclo(3.3.0)octanonen, herstellungsverfahren und anwendung als arzneimittel |
| HU212415B (en) * | 1989-08-25 | 1996-06-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new cyclic oxym derivatives and pharmaceutical compositions containing them as active components |
| US5665756A (en) * | 1994-08-03 | 1997-09-09 | Hoechst Marion Roussel, Inc. | Aminoalkyloximes useful in the treatment of depression and obsessive compulsive disorders |
| KR100533431B1 (ko) * | 1995-01-23 | 2006-05-03 | 다이이치 아스비오파마 가부시키가이샤 | 허혈성질환에기인하는증상의완화또는치료용약제및이에유용한화합물 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2832804A (en) * | 1958-04-29 | Production of i-aminoindan derivatives | ||
| US2712031A (en) * | 1953-10-27 | 1955-06-28 | Lasdon Foundation Inc | Monosubstituted salicylaldehyde alkoximes |
| US3060177A (en) * | 1957-11-11 | 1962-10-23 | Ciba Geigy Corp | O-(aminoalkyl)oxime derivatives of heterocyclic aldehydes and ketones |
| US3692835A (en) * | 1967-04-05 | 1972-09-19 | Jan Van Dijk | Pharmacologically active amino-ethyl oximes |
| US3951983A (en) * | 1970-11-10 | 1976-04-20 | Pfizer Inc. | Phenoxypropanolpiperazines |
| SE371193B (cg-RX-API-DMAC7.html) * | 1972-03-24 | 1974-11-11 | Kabi Ab | |
| US3954763A (en) * | 1972-04-10 | 1976-05-04 | Synthelabo | N-Metatrifluoromethylthiophenyl-piperazine |
| GB1415505A (en) * | 1972-06-01 | 1975-11-26 | Ici Ltd | Alkanolamine derivatives |
| SE397088B (sv) * | 1972-06-17 | 1977-10-17 | Sumitomo Chemical Co | Forfarande for framstellning av nya 2-propanolderivat |
| US4100282A (en) * | 1972-12-23 | 1978-07-11 | Boehringer Ingelheim Gmbh | N-Aryl-N'-(phenyl- or phenoxy-alkyl)-piperazines and salts thereof |
| GB1437868A (en) * | 1973-05-09 | 1976-06-03 | Synthelabo | Arylpiperazinoalkyl esters |
| US4207319A (en) * | 1973-10-19 | 1980-06-10 | Albert Rolland S.A. | Thienyl or furyl phenyl O-hetero amino alkyl oximes and use thereof |
| US3960956A (en) * | 1974-11-21 | 1976-06-01 | E. I. Du Pont De Nemours & Company | Antidepressant 1,1a,6,10b-tetrahydrodibenzo(a,e)-cyclo-propa(c) cyclohepten-6-substituted oximes |
| GB1474316A (en) * | 1975-02-12 | 1977-05-25 | Seperic | O-aminoalkyl oximes |
| DK149043C (da) * | 1976-01-27 | 1986-05-26 | Egyt Gyogyszervegyeszeti Gyar | Analogifremgangsmaade til fremstilling af 2-benzal- eller 2-benzyl-1-(aminoalkoxyimino)-cykloalkaner eller salte eller kvaternaere ammoniumderivater deraf |
| US4187220A (en) * | 1977-08-30 | 1980-02-05 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | New O-(3-amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same |
-
1976
- 1976-12-24 DE DE19762658938 patent/DE2658938A1/de not_active Withdrawn
-
1977
- 1977-12-19 NL NL7714054A patent/NL7714054A/xx not_active Application Discontinuation
- 1977-12-19 ES ES465204A patent/ES465204A1/es not_active Expired
- 1977-12-21 GB GB53220/77A patent/GB1543517A/en not_active Expired
- 1977-12-21 AU AU31811/77A patent/AU512353B2/en not_active Expired
- 1977-12-21 ZA ZA00777586A patent/ZA777586B/xx unknown
- 1977-12-22 SE SE7714685A patent/SE7714685L/xx not_active Application Discontinuation
- 1977-12-22 FI FI773903A patent/FI773903A7/fi not_active Application Discontinuation
- 1977-12-22 PT PT67444A patent/PT67444B/pt unknown
- 1977-12-22 GR GR55042A patent/GR70042B/el unknown
- 1977-12-22 DK DK575277A patent/DK575277A/da not_active Application Discontinuation
- 1977-12-22 AT AT924777A patent/AT360544B/de not_active IP Right Cessation
- 1977-12-22 IE IE2605/77A patent/IE46226B1/en unknown
- 1977-12-22 IL IL53674A patent/IL53674A/xx unknown
- 1977-12-23 HU HU77HO2037A patent/HU177453B/hu unknown
- 1977-12-23 IT IT31206/77A patent/IT1089233B/it active
- 1977-12-23 NO NO774456A patent/NO774456L/no unknown
- 1977-12-23 FR FR7739023A patent/FR2375225A1/fr active Granted
- 1977-12-23 BE BE183831A patent/BE862303A/xx unknown
- 1977-12-23 CA CA293,826A patent/CA1105933A/en not_active Expired
- 1977-12-23 JP JP15547977A patent/JPS5379875A/ja active Pending
- 1977-12-23 LU LU78770A patent/LU78770A1/xx unknown
- 1977-12-24 PL PL1977214670A patent/PL112153B1/pl unknown
- 1977-12-24 PL PL1977214671A patent/PL111792B1/pl unknown
- 1977-12-24 PL PL1977203359A patent/PL110753B1/pl unknown
-
1978
- 1978-05-04 ES ES469455A patent/ES469455A1/es not_active Expired
- 1978-05-04 ES ES469456A patent/ES469456A1/es not_active Expired
-
1979
- 1979-02-28 JP JP2205679A patent/JPS54141784A/ja active Pending
-
1980
- 1980-05-19 US US06/150,705 patent/US4328227A/en not_active Expired - Lifetime
- 1980-06-12 JP JP7845480A patent/JPS5695166A/ja active Pending
- 1980-06-12 JP JP7845580A patent/JPS5677275A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0617012A1 (de) * | 1993-03-02 | 1994-09-28 | BASF Aktiengesellschaft | Beta-Hydroxyoximether und bei Raumtemperatur mit beta-Hydroxyoximethern vernetzbare Dispersionen oder Lösungen |
| US5527944A (en) * | 1993-03-02 | 1996-06-18 | Basf Aktiengesellschaft | β-hydroxyoxime ethers and solutions or dispersions crosslinkable at room temperature with β-hydroxyoxime ethers |
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Legal Events
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| OAP | Request for examination filed | ||
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| 8130 | Withdrawal |