SE450894B - Karboximidderivat, forfarande for framstellning derav och farmaceutisk komposition - Google Patents
Karboximidderivat, forfarande for framstellning derav och farmaceutisk kompositionInfo
- Publication number
- SE450894B SE450894B SE8203272A SE8203272A SE450894B SE 450894 B SE450894 B SE 450894B SE 8203272 A SE8203272 A SE 8203272A SE 8203272 A SE8203272 A SE 8203272A SE 450894 B SE450894 B SE 450894B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- formula
- propyl
- pyridyl
- piperazin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical class C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 cinnamoyl Chemical group 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 101150009274 nhr-1 gene Proteins 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 117
- 238000000921 elemental analysis Methods 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 229960002317 succinimide Drugs 0.000 description 14
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JFUOAGBSDGCVES-UHFFFAOYSA-N 3-but-2-enyl-4-methylpyrrolidine-2,5-dione Chemical compound CC=CCC1C(C)C(=O)NC1=O JFUOAGBSDGCVES-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- MDDVEUPIZIKAJU-UHFFFAOYSA-N 3-methyl-4-pent-2-enylpyrrolidine-2,5-dione Chemical compound CCC=CCC1C(C)C(=O)NC1=O MDDVEUPIZIKAJU-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- SJHAYDPFTZNBEN-SPIKMXEPSA-N OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CC=CCC1C(C)C(=O)NC1=O Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CC=CCC1C(C)C(=O)NC1=O SJHAYDPFTZNBEN-SPIKMXEPSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 2
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- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
- C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
-
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D401/14—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 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56080866A JPS57197265A (en) | 1981-05-29 | 1981-05-29 | Carboxylic acid imide derivative, its preparation and medicament containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8203272L SE8203272L (sv) | 1982-11-30 |
| SE450894B true SE450894B (sv) | 1987-08-10 |
Family
ID=13730258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8203272A SE450894B (sv) | 1981-05-29 | 1982-05-26 | Karboximidderivat, forfarande for framstellning derav och farmaceutisk komposition |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4479954A (en, 2012) |
| JP (1) | JPS57197265A (en, 2012) |
| KR (1) | KR870001027B1 (en, 2012) |
| BE (1) | BE893378A (en, 2012) |
| CA (1) | CA1211436A (en, 2012) |
| CH (1) | CH649287A5 (en, 2012) |
| DE (1) | DE3220262A1 (en, 2012) |
| DK (1) | DK241982A (en, 2012) |
| ES (3) | ES512642A0 (en, 2012) |
| FR (1) | FR2506771A1 (en, 2012) |
| GB (1) | GB2101590B (en, 2012) |
| IT (1) | IT1151781B (en, 2012) |
| NL (1) | NL8202173A (en, 2012) |
| PH (3) | PH19837A (en, 2012) |
| SE (1) | SE450894B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507303A (en) * | 1981-12-22 | 1985-03-26 | Sumitomo Chemical Company, Limited | Succinimide derivatives, compositions and method of use |
| US4641251A (en) * | 1982-02-16 | 1987-02-03 | Inoue-Japax Research Incorporated | Robot |
| JPS5976059A (ja) * | 1982-10-21 | 1984-04-28 | Sumitomo Chem Co Ltd | 環状イミド誘導体及びその酸付加塩 |
| JPS5995267A (ja) * | 1982-11-25 | 1984-06-01 | Eisai Co Ltd | カルボン酸イミド誘導体およびその製造方法 |
| DE3321969A1 (de) * | 1983-06-18 | 1984-12-20 | Troponwerke GmbH & Co KG, 5000 Köln | 2-pyrimidinyl-1-piperazin-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4562255A (en) * | 1984-03-30 | 1985-12-31 | American Home Products Corporation | Substituted bi-alicyclic imides |
| JPH0625181B2 (ja) * | 1985-03-27 | 1994-04-06 | 住友製薬株式会社 | 新規なイミド誘導体 |
| JPS61238784A (ja) * | 1985-04-17 | 1986-10-24 | Sumitomo Seiyaku Kk | コハク酸イミド誘導体及びその酸付加塩 |
| JP2660407B2 (ja) * | 1986-09-26 | 1997-10-08 | 住友製薬株式会社 | 新規なイミド誘導体 |
| DE8630918U1 (de) * | 1986-11-18 | 1987-11-05 | Fritz Bauer + Söhne oHG, 8503 Altdorf | Längenverstellbare Gasfeder für höhenverstellbare Stühle, Tische od.dgl. |
| US4804751A (en) * | 1987-06-30 | 1989-02-14 | American Home Products Corporation | Polycyclic hydrocarbon succinimides with psychotropic activity |
| US5053508A (en) * | 1990-03-09 | 1991-10-01 | American Home Products Corporation | Fused heterotricyclic imides with psychotropic activity and intermedrates thereof |
| US6083950A (en) * | 1997-11-13 | 2000-07-04 | Ranbaxy Laboratories Limited | 1-(4-arylpiperazin-1-yl)-ω-[n-(α,ω-dicarboximido)]-alka nes useful as uro-selective α1-adrenoceptor blockers |
| WO2000005205A1 (en) * | 1998-07-21 | 2000-02-03 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives useful as uroselective alpha1-adrenoceptor blockers |
| WO2000005206A1 (en) * | 1998-07-21 | 2000-02-03 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives useful as uro-selective alpha-1-adrenoceptor blockers |
| EP1339682A1 (en) | 2000-11-30 | 2003-09-03 | Ranbaxy Laboratories, Ltd. | 1,4-disubstituted piperazine derivatives useful as uro-selective $g(a)1-adrenoceptor blockers |
| CN1787995A (zh) * | 2002-04-08 | 2006-06-14 | 兰贝克赛实验室有限公司 | 用作尿－选择性α－1A肾上腺素受体阻滞剂的α,w－二羧酰亚胺衍生物 |
| US7605260B2 (en) | 2003-07-29 | 2009-10-20 | Dainippon Sumitomo Pharma Co., Ltd. | Process for producing imide compound |
| WO2005118537A2 (en) * | 2004-05-31 | 2005-12-15 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives as adrenergic receptor antagonists |
| US20060247249A1 (en) * | 2005-11-16 | 2006-11-02 | Mohammad Salman | Carboximide derivatives as useful uro-selective alpha-1a adrenoceptor blockers |
| WO2025141607A1 (en) * | 2023-12-26 | 2025-07-03 | Heterochem Innotech Private Limited | Novel phthalimide compounds or tissue/cell regeneration and compositions comprising thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3126395A (en) * | 1964-03-24 | Chj czhs | ||
| US3126396A (en) * | 1964-03-24 | Chiih | ||
| US2343198A (en) * | 1940-04-03 | 1944-02-29 | Abbott Lab | Nu-alkamine substituted derivatives of phthalimide |
| US3198798A (en) * | 1962-11-02 | 1965-08-03 | Sterling Drug Inc | Phthalimido- and isoindolinyl-alkylpiperazines and their preparation |
| US3563986A (en) * | 1965-10-12 | 1971-02-16 | Ernst Frankus | 4 - phthalimido - n - heterocyclic amino methyl or piperidino hydrazino piperidine diones 2,6 |
| US3579524A (en) * | 1968-06-05 | 1971-05-18 | Miles Lab | 2-aminoalkyl derivatives of phthalimidines |
| US3850921A (en) * | 1972-09-20 | 1974-11-26 | I Matuo | Derivatives of 2,3-norbornanedicarboxamide |
| US3936449A (en) * | 1974-04-11 | 1976-02-03 | Sadao Ohki | Anti-arrhythmic agents |
| US3980667A (en) * | 1975-03-05 | 1976-09-14 | Bristol-Myers Company | Anti-arrhythmic 5-endo-substituted oxy-N-(aminoloweralkyl)bicycle [2.2.2.]oc |
| US4018767A (en) * | 1975-05-22 | 1977-04-19 | Bristol-Myers Company | Anti-arrhythmic agents |
| US4070465A (en) * | 1976-06-24 | 1978-01-24 | E. R. Squibb & Sons, Inc. | Various 2-(substituted piperazinyl)-1H-benz [de]isoquinoline-1,3 (2H) -diones |
| US4139533A (en) * | 1976-08-19 | 1979-02-13 | Bristol-Myers Company | Bicyclo[2,2,1]heptane-2,3-diendo carboxylic acid imide esters of quinoline carboxylic acid |
-
1981
- 1981-05-29 JP JP56080866A patent/JPS57197265A/ja active Granted
-
1982
- 1982-05-26 SE SE8203272A patent/SE450894B/sv not_active IP Right Cessation
- 1982-05-27 NL NL8202173A patent/NL8202173A/nl not_active Application Discontinuation
- 1982-05-27 US US06/382,792 patent/US4479954A/en not_active Expired - Fee Related
- 1982-05-28 CA CA000403984A patent/CA1211436A/en not_active Expired
- 1982-05-28 FR FR8209376A patent/FR2506771A1/fr active Granted
- 1982-05-28 ES ES512642A patent/ES512642A0/es active Granted
- 1982-05-28 CH CH3333/82A patent/CH649287A5/de not_active IP Right Cessation
- 1982-05-28 IT IT21563/82A patent/IT1151781B/it active
- 1982-05-28 DK DK241982A patent/DK241982A/da not_active Application Discontinuation
- 1982-05-28 PH PH27367A patent/PH19837A/en unknown
- 1982-05-28 DE DE19823220262 patent/DE3220262A1/de not_active Withdrawn
- 1982-05-29 KR KR8202402A patent/KR870001027B1/ko not_active Expired
- 1982-06-01 BE BE0/208242A patent/BE893378A/fr not_active IP Right Cessation
- 1982-06-01 GB GB08215992A patent/GB2101590B/en not_active Expired
-
1983
- 1983-06-13 ES ES523205A patent/ES8503343A1/es not_active Expired
-
1984
- 1984-01-09 PH PH30076A patent/PH19291A/en unknown
- 1984-01-09 PH PH30077A patent/PH19272A/en unknown
- 1984-11-16 ES ES537721A patent/ES537721A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH649287A5 (de) | 1985-05-15 |
| ES523205A0 (es) | 1985-02-16 |
| DE3220262A1 (de) | 1982-12-16 |
| ES8308548A1 (es) | 1983-09-01 |
| PH19291A (en) | 1986-03-04 |
| GB2101590A (en) | 1983-01-19 |
| BE893378A (fr) | 1982-12-01 |
| DK241982A (da) | 1982-11-30 |
| NL8202173A (nl) | 1982-12-16 |
| US4479954A (en) | 1984-10-30 |
| KR830010103A (ko) | 1983-12-26 |
| ES8601156A1 (es) | 1985-10-16 |
| KR870001027B1 (ko) | 1987-05-25 |
| JPS57197265A (en) | 1982-12-03 |
| IT1151781B (it) | 1986-12-24 |
| FR2506771A1 (fr) | 1982-12-03 |
| FR2506771B1 (en, 2012) | 1985-03-01 |
| ES8503343A1 (es) | 1985-02-16 |
| JPH0229671B2 (en, 2012) | 1990-07-02 |
| GB2101590B (en) | 1985-06-19 |
| ES537721A0 (es) | 1985-10-16 |
| PH19272A (en) | 1986-02-21 |
| PH19837A (en) | 1986-07-22 |
| ES512642A0 (es) | 1983-09-01 |
| SE8203272L (sv) | 1982-11-30 |
| CA1211436A (en) | 1986-09-16 |
| IT8221563A0 (it) | 1982-05-28 |
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