LV10575B - Isoxazole-4-carboxamides and hydroxyalkylidene-cyanoacetamides, drugs containing these compounds and use of such drugs - Google Patents
Isoxazole-4-carboxamides and hydroxyalkylidene-cyanoacetamides, drugs containing these compounds and use of such drugs Download PDFInfo
- Publication number
- LV10575B LV10575B LVP-93-310A LV930310A LV10575B LV 10575 B LV10575 B LV 10575B LV 930310 A LV930310 A LV 930310A LV 10575 B LV10575 B LV 10575B
- Authority
- LV
- Latvia
- Prior art keywords
- alkyl
- halogen
- mono
- atoms
- bromine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 239000003814 drug Substances 0.000 title claims abstract description 23
- QBPXGTUBZXXKJO-UHFFFAOYSA-N 1,2-oxazole-4-carboxamide Chemical class NC(=O)C=1C=NOC=1 QBPXGTUBZXXKJO-UHFFFAOYSA-N 0.000 title abstract description 8
- 229940079593 drug Drugs 0.000 title 2
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 7
- 208000025747 Rheumatic disease Diseases 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 179
- 229910052736 halogen Inorganic materials 0.000 claims description 142
- 150000002367 halogens Chemical class 0.000 claims description 142
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 140
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 140
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 140
- 229910052794 bromium Inorganic materials 0.000 claims description 140
- 239000000460 chlorine Substances 0.000 claims description 140
- 229910052801 chlorine Inorganic materials 0.000 claims description 140
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 138
- 229910052731 fluorine Inorganic materials 0.000 claims description 138
- 239000011737 fluorine Substances 0.000 claims description 138
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 239000001257 hydrogen Substances 0.000 claims description 101
- 150000002431 hydrogen Chemical class 0.000 claims description 77
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- -1 methylenedioxy group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 229910052740 iodine Inorganic materials 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 239000011630 iodine Substances 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 208000032839 leukemia Diseases 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 206010039491 Sarcoma Diseases 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 150000003931 anilides Chemical class 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 208000022766 lymph node neoplasm Diseases 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- VKXYORVLYJXLSK-UHFFFAOYSA-N 5-methyl-n-(4-methylsulfonylphenyl)-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)S(C)(=O)=O)=C1C VKXYORVLYJXLSK-UHFFFAOYSA-N 0.000 claims description 3
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- NWOVTJSCRMZLMM-UHFFFAOYSA-N n-(1h-indazol-6-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C3NN=CC3=CC=2)=C1C NWOVTJSCRMZLMM-UHFFFAOYSA-N 0.000 claims description 3
- NCJHFNRNOOGXMN-UHFFFAOYSA-N n-(1h-indol-5-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C3C=CNC3=CC=2)=C1C NCJHFNRNOOGXMN-UHFFFAOYSA-N 0.000 claims description 3
- AFIFBOMOIFYWFT-UHFFFAOYSA-N n-(4,6-dimethylpyridin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=C(C)C=C(C)C=2)=C1C AFIFBOMOIFYWFT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 201000000849 skin cancer Diseases 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- RXSNFDWFKNKMKV-UHFFFAOYSA-N n-(1h-indazol-5-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C3C=NNC3=CC=2)=C1C RXSNFDWFKNKMKV-UHFFFAOYSA-N 0.000 claims description 2
- RLGIIWFUFLEEEX-UHFFFAOYSA-N n-(4,6-dimethylpyrimidin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=C(C)C=C(C)N=2)=C1C RLGIIWFUFLEEEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- PVVLPBGEJWCJPE-UHFFFAOYSA-N 2-pentyl-1,3-oxazole-4-carboxylic acid Chemical compound CCCCCc1nc(co1)C(O)=O PVVLPBGEJWCJPE-UHFFFAOYSA-N 0.000 claims 1
- BPOJESSTIKFRED-UHFFFAOYSA-N 5-ethyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound C1(=CC=CC=C1)C1=NOC(=C1C(=O)N)CC BPOJESSTIKFRED-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000002844 melting Methods 0.000 description 84
- 230000008018 melting Effects 0.000 description 84
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- 150000003254 radicals Chemical class 0.000 description 16
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- 239000002609 medium Substances 0.000 description 15
- ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 13
- RFXIFHIHWYTKIG-UHFFFAOYSA-N 5-ethyl-1,2-oxazole-4-carbonyl chloride Chemical compound CCC=1ON=CC=1C(Cl)=O RFXIFHIHWYTKIG-UHFFFAOYSA-N 0.000 description 12
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/40—Y being a hydrogen or a carbon 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
- C07D213/60—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
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Air Conditioning Control Device (AREA)
- Indole Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4016178 | 1990-05-18 | ||
DE4017020 | 1990-05-26 | ||
DE4017043 | 1990-05-26 | ||
PCT/EP1990/001800 WO1991017748A1 (de) | 1990-05-18 | 1990-10-24 | Isoxazol-4-carbonsäureamide und hydroxyalkyliden-cyanessigsäureamide, diese verbindungen enthaltende arzneimittel und deren verwendung |
Publications (2)
Publication Number | Publication Date |
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LV10575A LV10575A (lv) | 1995-04-20 |
LV10575B true LV10575B (en) | 1996-04-20 |
Family
ID=27201216
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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LVP-93-310A LV10575B (en) | 1990-05-18 | 1993-05-07 | Isoxazole-4-carboxamides and hydroxyalkylidene-cyanoacetamides, drugs containing these compounds and use of such drugs |
Country Status (28)
Country | Link |
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US (2) | US5494911A (cs) |
EP (1) | EP0527736B1 (cs) |
JP (3) | JP2995086B2 (cs) |
KR (1) | KR100188801B1 (cs) |
CN (1) | CN1051074C (cs) |
AT (1) | ATE151633T1 (cs) |
AU (2) | AU649421B2 (cs) |
BR (1) | BR9008022A (cs) |
CA (1) | CA2083179C (cs) |
CY (1) | CY2123B1 (cs) |
CZ (4) | CZ290474B6 (cs) |
DE (1) | DE59010701D1 (cs) |
DK (1) | DK0527736T3 (cs) |
ES (1) | ES2102367T3 (cs) |
FI (1) | FI105683B (cs) |
GR (1) | GR3023638T3 (cs) |
HU (1) | HU222234B1 (cs) |
IE (1) | IE911694A1 (cs) |
IL (1) | IL98163A (cs) |
LV (1) | LV10575B (cs) |
NO (1) | NO180118C (cs) |
NZ (1) | NZ238165A (cs) |
PT (1) | PT97689B (cs) |
RU (2) | RU2084223C1 (cs) |
SK (3) | SK281317B6 (cs) |
TW (2) | TW211558B (cs) |
WO (1) | WO1991017748A1 (cs) |
YU (1) | YU48765B (cs) |
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GB9313365D0 (en) * | 1993-06-29 | 1993-08-11 | Roussel Lab Ltd | Chemical compounds |
DE4323636A1 (de) * | 1993-07-15 | 1995-01-19 | Hoechst Ag | Arzneistoffzubereitungen aus umhüllten, schwerstwasserlöslichen Arzneistoffen für Inhalationsarzneiformen und Verfahren zu ihrer Herstellung |
GB9322781D0 (en) * | 1993-11-04 | 1993-12-22 | Roussel Lab Ltd | Aromatic amides |
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DE19547648A1 (de) * | 1995-12-20 | 1997-06-26 | Hoechst Ag | Zubereitung, enthaltend High Density Lipoproteine und Crotonsäureamidderivate |
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US6011051A (en) * | 1996-07-31 | 2000-01-04 | Hoechst Aktiengesellschaft | Use of isoxazole and crotonamide derivatives for the modulation of apoptosis |
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DE19702988A1 (de) * | 1997-01-28 | 1998-07-30 | Hoechst Ag | Isoxazol- und Crotonsäureamidderivate und deren Verwendung als Arzneimittel und Diagnostika |
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ES448386A1 (es) * | 1975-06-05 | 1978-04-16 | Hoechst Ag | Procedimiento para la preparacion de anilidas de acido 5-me-til-isoxazol-4-carboxilico. |
NL186239B (nl) * | 1975-06-05 | Hoechst Ag | Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze. | |
DE2524959C2 (de) * | 1975-06-05 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | 5-Methyl-isoxazol-4-carbonsäureanilide, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel |
DE2557003A1 (de) * | 1975-12-18 | 1977-06-23 | Hoechst Ag | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
DE2555789A1 (de) * | 1975-12-11 | 1977-07-07 | Hoechst Ag | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
DE2655009A1 (de) * | 1976-12-04 | 1978-06-15 | Hoechst Ag | Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
DE2854439A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Ein isoxazolderivat, verfahren zu seiner herstellung, diese verbindung enthaltende mittel und verwendung |
DE3405727A1 (de) * | 1984-02-17 | 1985-08-22 | Hoechst Ag, 6230 Frankfurt | Isoxazol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3534440A1 (de) * | 1985-09-27 | 1987-04-02 | Hoechst Ag | Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes |
GB8619432D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
GB8619433D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
US4816467A (en) * | 1987-01-09 | 1989-03-28 | Farmitalia Carlo Erba S.R.L | Heteroaryl 3-oxo-propanenitrile derivatives, pharmaceutical compositions and use |
-
1990
- 1990-10-24 DE DE59010701T patent/DE59010701D1/de not_active Expired - Lifetime
- 1990-10-24 EP EP90915462A patent/EP0527736B1/de not_active Expired - Lifetime
- 1990-10-24 BR BR909008022A patent/BR9008022A/pt not_active Application Discontinuation
- 1990-10-24 RU RU9092016445A patent/RU2084223C1/ru active
- 1990-10-24 KR KR1019920702895A patent/KR100188801B1/ko not_active Expired - Lifetime
- 1990-10-24 AU AU65468/90A patent/AU649421B2/en not_active Expired
- 1990-10-24 DK DK90915462.7T patent/DK0527736T3/da active
- 1990-10-24 JP JP2514415A patent/JP2995086B2/ja not_active Expired - Lifetime
- 1990-10-24 ES ES90915462T patent/ES2102367T3/es not_active Expired - Lifetime
- 1990-10-24 RU RU94033835A patent/RU2142937C1/ru active
- 1990-10-24 AT AT90915462T patent/ATE151633T1/de not_active IP Right Cessation
- 1990-10-24 CA CA002083179A patent/CA2083179C/en not_active Expired - Lifetime
- 1990-10-24 US US07/938,048 patent/US5494911A/en not_active Expired - Lifetime
- 1990-10-24 HU HU9203619A patent/HU222234B1/hu active IP Right Grant
- 1990-10-24 WO PCT/EP1990/001800 patent/WO1991017748A1/de active IP Right Grant
- 1990-10-27 TW TW081101406A patent/TW211558B/zh active
- 1990-10-27 TW TW079109110A patent/TW205004B/zh active
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1991
- 1991-05-16 IL IL9816391A patent/IL98163A/en not_active IP Right Cessation
- 1991-05-16 SK SK1376-98A patent/SK281317B6/sk not_active IP Right Cessation
- 1991-05-16 CZ CS19911450A patent/CZ290474B6/cs not_active IP Right Cessation
- 1991-05-16 PT PT97689A patent/PT97689B/pt not_active IP Right Cessation
- 1991-05-16 SK SK542-99A patent/SK281318B6/sk not_active IP Right Cessation
- 1991-05-16 NZ NZ238165A patent/NZ238165A/en not_active IP Right Cessation
- 1991-05-16 SK SK1450-91A patent/SK281316B6/sk not_active IP Right Cessation
- 1991-05-16 CN CN91103182A patent/CN1051074C/zh not_active Expired - Lifetime
- 1991-05-17 IE IE169491A patent/IE911694A1/en not_active IP Right Cessation
- 1991-05-20 YU YU88491A patent/YU48765B/sr unknown
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1992
- 1992-11-17 NO NO924433A patent/NO180118C/no not_active IP Right Cessation
- 1992-11-17 FI FI925211A patent/FI105683B/fi active
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1993
- 1993-05-07 LV LVP-93-310A patent/LV10575B/en unknown
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1994
- 1994-03-23 AU AU57992/94A patent/AU662465B2/en not_active Expired
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1995
- 1995-06-07 US US08/476,278 patent/US5532259A/en not_active Expired - Lifetime
- 1995-08-24 CZ CZ19952176A patent/CZ290717B6/cs not_active IP Right Cessation
- 1995-11-23 CZ CZ19953091A patent/CZ290736B6/cs not_active IP Right Cessation
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1997
- 1997-05-30 GR GR970401284T patent/GR3023638T3/el unknown
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1998
- 1998-09-29 CY CY9800032A patent/CY2123B1/xx unknown
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1999
- 1999-03-01 JP JP05210899A patent/JP3233610B2/ja not_active Expired - Lifetime
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