ZA200605938B - Cinnamic amides, process for their preparation, and pharmaceutical compositions containing them - Google Patents
Cinnamic amides, process for their preparation, and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- ZA200605938B ZA200605938B ZA200605938A ZA200605938A ZA200605938B ZA 200605938 B ZA200605938 B ZA 200605938B ZA 200605938 A ZA200605938 A ZA 200605938A ZA 200605938 A ZA200605938 A ZA 200605938A ZA 200605938 B ZA200605938 B ZA 200605938B
- Authority
- ZA
- South Africa
- Prior art keywords
- chloro
- hydrogen
- piperazine
- trans
- prop
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 3
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- -1 chloro, bromo, methyl Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 150000001408 amides Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 230000003463 hyperproliferative effect Effects 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- CXJXXFYLNIOWLV-VVUIVXFESA-N (e)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-(3-methoxy-4-methylphenyl)prop-2-en-1-one Chemical compound C1=C(C)C(OC)=CC(\C=C\C(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 CXJXXFYLNIOWLV-VVUIVXFESA-N 0.000 claims description 2
- ZKJAEWHXWOERTF-CFMJQPPZSA-N (e)-3-(4-bromo-3,5-dimethoxyphenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound COC1=C(Br)C(OC)=CC(\C=C\C(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 ZKJAEWHXWOERTF-CFMJQPPZSA-N 0.000 claims description 2
- NCBBCDMAFMADSJ-MYGHVRAUSA-N (e)-3-(4-bromophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=CC(Br)=CC=2)N1CC1=CC=C(F)C=C1 NCBBCDMAFMADSJ-MYGHVRAUSA-N 0.000 claims description 2
- MUODIXPAAMFKLO-QZKWLWDQSA-N (e)-3-(4-chloro-3-methoxyphenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 MUODIXPAAMFKLO-QZKWLWDQSA-N 0.000 claims description 2
- VDPCDHQHRFYPMO-MYGHVRAUSA-N (e)-3-(4-chlorophenyl)-1-[(2s,5r)-4-[(4-chlorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=CC(Cl)=CC=2)N1CC1=CC=C(Cl)C=C1 VDPCDHQHRFYPMO-MYGHVRAUSA-N 0.000 claims description 2
- NUGVIURZPVNENF-MYGHVRAUSA-N (e)-3-(4-chlorophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 NUGVIURZPVNENF-MYGHVRAUSA-N 0.000 claims description 2
- 229930105110 Cyclosporin A Natural products 0.000 claims description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 2
- 108010036949 Cyclosporine Proteins 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 229960001265 ciclosporin Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- HKPZGRGBMIHGFA-PHGPQXGHSA-N (e)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-(4-nitro-2,1,3-benzothiadiazol-5-yl)prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C2=C(C3=NSN=C3C=C2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 HKPZGRGBMIHGFA-PHGPQXGHSA-N 0.000 claims 1
- XVPGKJHJPPXKGX-ZLAMNEIASA-N (e)-3-(3,4-dichlorophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(Cl)C(Cl)=CC=2)N1CC1=CC=C(F)C=C1 XVPGKJHJPPXKGX-ZLAMNEIASA-N 0.000 claims 1
- SRTPIDXNOUIPFY-ZLAMNEIASA-N (e)-3-(3-bromo-4-chlorophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(Br)C(Cl)=CC=2)N1CC1=CC=C(F)C=C1 SRTPIDXNOUIPFY-ZLAMNEIASA-N 0.000 claims 1
- AKEAEBKCZNBVBP-ZRJDUIELSA-N (e)-3-(4-bromo-2,1,3-benzothiadiazol-6-yl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C2=CC3=NSN=C3C(Br)=C2)N1CC1=CC=C(F)C=C1 AKEAEBKCZNBVBP-ZRJDUIELSA-N 0.000 claims 1
- UUOPZGHTDZVTTF-ZLAMNEIASA-N (e)-3-(4-bromo-3-chlorophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(Cl)C(Br)=CC=2)N1CC1=CC=C(F)C=C1 UUOPZGHTDZVTTF-ZLAMNEIASA-N 0.000 claims 1
- TXKACNZTVPBGTE-ZRJDUIELSA-N (e)-3-(4-chloro-2,1,3-benzothiadiazol-6-yl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C2=CC3=NSN=C3C(Cl)=C2)N1CC1=CC=C(F)C=C1 TXKACNZTVPBGTE-ZRJDUIELSA-N 0.000 claims 1
- UTTQLRLQFCIJKS-ZLAMNEIASA-N (e)-3-(4-chloro-3-nitrophenyl)-1-[(2s,5r)-4-[(4-chlorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)N1CC1=CC=C(Cl)C=C1 UTTQLRLQFCIJKS-ZLAMNEIASA-N 0.000 claims 1
- LLEHWXJRYJBMAG-ZLAMNEIASA-N (e)-3-(4-chloro-3-nitrophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 LLEHWXJRYJBMAG-ZLAMNEIASA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 4
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 4
- 102000001327 Chemokine CCL5 Human genes 0.000 description 4
- 108010055166 Chemokine CCL5 Proteins 0.000 description 4
- 102000019034 Chemokines Human genes 0.000 description 4
- 108010012236 Chemokines Proteins 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- NSMWYRLQHIXVAP-OLQVQODUSA-N (2r,5s)-2,5-dimethylpiperazine Chemical class C[C@H]1CN[C@H](C)CN1 NSMWYRLQHIXVAP-OLQVQODUSA-N 0.000 description 1
- DWIXPCRDOSQHKC-MSOLQXFVSA-N (E)-1-[(2S,5R)-4-[(4-chlorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-(4-methyl-3-nitrophenyl)prop-2-en-1-one Chemical compound ClC1=CC=C(CN2C[C@@H](N(C[C@H]2C)C(C=CC2=CC(=C(C=C2)C)[N+](=O)[O-])=O)C)C=C1 DWIXPCRDOSQHKC-MSOLQXFVSA-N 0.000 description 1
- KUQMPNNVWBPJJM-RWTNSZMUSA-N (e)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-(4-methyl-3-nitrophenyl)prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(C(C)=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 KUQMPNNVWBPJJM-RWTNSZMUSA-N 0.000 description 1
- ZRVSRURMLOILMM-ZLAMNEIASA-N (e)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-[4-nitro-3-(trifluoromethyl)phenyl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=C(C(=CC=2)[N+]([O-])=O)C(F)(F)F)N1CC1=CC=C(F)C=C1 ZRVSRURMLOILMM-ZLAMNEIASA-N 0.000 description 1
- ZFIWQGNVJAXTOB-ALHCXDLNSA-N (e)-3-(2,4-dimethylphenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C(=CC(C)=CC=2)C)N1CC1=CC=C(F)C=C1 ZFIWQGNVJAXTOB-ALHCXDLNSA-N 0.000 description 1
- WOFPYQQULNYUMT-ZRJDUIELSA-N (e)-3-(4-bromo-2,1,3-benzoxadiazol-6-yl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C2=CC3=NON=C3C(Br)=C2)N1CC1=CC=C(F)C=C1 WOFPYQQULNYUMT-ZRJDUIELSA-N 0.000 description 1
- MTVJXQQTZOCTJH-MYGHVRAUSA-N (e)-3-(4-bromophenyl)-1-[(2s,5r)-4-[(4-chlorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]prop-2-en-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C=CC(Br)=CC=2)N1CC1=CC=C(Cl)C=C1 MTVJXQQTZOCTJH-MYGHVRAUSA-N 0.000 description 1
- PNDFYDVWDDXEHK-UHFFFAOYSA-N 1-(2-benzylpiperazin-1-yl)-3-phenylprop-2-en-1-one Chemical class C1CNCC(CC=2C=CC=CC=2)N1C(=O)C=CC1=CC=CC=C1 PNDFYDVWDDXEHK-UHFFFAOYSA-N 0.000 description 1
- BBDMDSWCRPBOGN-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]-3-(2,4-dichlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1CN1CCN(C(=O)C=CC=2C(=CC(Cl)=CC=2)Cl)CC1 BBDMDSWCRPBOGN-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- ZQXXBLADSLNAAT-UHFFFAOYSA-N 1-piperazin-1-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical class COC1=C(OC)C(OC)=CC(C=CC(=O)N2CCNCC2)=C1 ZQXXBLADSLNAAT-UHFFFAOYSA-N 0.000 description 1
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical class CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 1
- HVTUHSABWJPWNK-UHFFFAOYSA-N 2-[2-chloro-5-[3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-4-(methylcarbamoyl)phenoxy]-2-methylpropanoic acid Chemical compound CNC(=O)C1=CC(Cl)=C(OC(C)(C)C(O)=O)C=C1OCC(O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 HVTUHSABWJPWNK-UHFFFAOYSA-N 0.000 description 1
- GCSUHUNWANLMJR-UHFFFAOYSA-N 2-methyl-3-[4-(3-phenylprop-2-enoyl)piperazin-1-yl]benzoic acid Chemical class C1=CC=C(C(O)=O)C(C)=C1N1CCN(C(=O)C=CC=2C=CC=CC=2)CC1 GCSUHUNWANLMJR-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0400440A SE0400440D0 (sv) | 2004-02-25 | 2004-02-25 | Novel Cinnamic Amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605938B true ZA200605938B (en) | 2007-10-31 |
Family
ID=31989606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605938A ZA200605938B (en) | 2004-02-25 | 2004-11-23 | Cinnamic amides, process for their preparation, and pharmaceutical compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20050192289A1 (ja) |
| EP (1) | EP1718628A1 (ja) |
| JP (1) | JP2007523919A (ja) |
| CN (1) | CN1918139A (ja) |
| AU (1) | AU2004316217A1 (ja) |
| CA (1) | CA2552433A1 (ja) |
| SE (1) | SE0400440D0 (ja) |
| WO (1) | WO2005080362A1 (ja) |
| ZA (1) | ZA200605938B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011097797A1 (zh) * | 2010-02-10 | 2011-08-18 | Peng Jinlian | 多酚丙烯酸衍生物，其制备方法以及在制备药物中的应用 |
| US9776979B2 (en) * | 2013-09-26 | 2017-10-03 | Sanford-Burnham Medical Research Institute | EBI2 modulators |
| MX2017012009A (es) * | 2015-03-24 | 2018-06-06 | Shanghai Yingli Pharm Co Ltd | Derivado de un anillo condensado y metodo de preparacion, compuesto intermedio, composicion farmaceutica y uso del mismo. |
| CN107151234A (zh) * | 2017-05-15 | 2017-09-12 | 重庆康刻尔制药有限公司 | 一种伊拉地平杂质ⅰ的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4368199A (en) * | 1980-01-21 | 1983-01-11 | Delalande S.A. | Novel derivatives of 3,4,5-trimethoxy cinnamoyl piperazine, their salts, the process for preparing the same and their application in therapeutics |
| DE3139970A1 (de) * | 1981-10-08 | 1983-04-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| JPS6219577A (ja) * | 1985-07-16 | 1987-01-28 | Kanebo Ltd | 新規なベンジルピペラジン誘導体および該化合物を有効成分とする医薬組成物 |
| FR2725445B1 (fr) * | 1994-10-10 | 1996-10-31 | Adir | Nouveaux derives a structure 1-arylalkenyl 4-aryl alkyl piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6207665B1 (en) * | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
| DE10040016A1 (de) * | 2000-08-16 | 2002-02-28 | Boehringer Ingelheim Pharma | Neue beta-Amyloid Inhibitoren, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| GB0224917D0 (en) * | 2002-10-25 | 2002-12-04 | Novartis Ag | Organic compounds |
-
2004
- 2004-02-25 SE SE0400440A patent/SE0400440D0/xx unknown
- 2004-11-23 JP JP2007500070A patent/JP2007523919A/ja active Pending
- 2004-11-23 US US10/995,036 patent/US20050192289A1/en not_active Abandoned
- 2004-11-23 CA CA002552433A patent/CA2552433A1/en not_active Abandoned
- 2004-11-23 CN CNA2004800419749A patent/CN1918139A/zh active Pending
- 2004-11-23 AU AU2004316217A patent/AU2004316217A1/en not_active Abandoned
- 2004-11-23 WO PCT/EP2004/053056 patent/WO2005080362A1/en active Application Filing
- 2004-11-23 EP EP04821684A patent/EP1718628A1/en not_active Withdrawn
- 2004-11-23 ZA ZA200605938A patent/ZA200605938B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005080362A1 (en) | 2005-09-01 |
| JP2007523919A (ja) | 2007-08-23 |
| US20050192289A1 (en) | 2005-09-01 |
| CA2552433A1 (en) | 2005-09-01 |
| SE0400440D0 (sv) | 2004-02-25 |
| EP1718628A1 (en) | 2006-11-08 |
| CN1918139A (zh) | 2007-02-21 |
| AU2004316217A1 (en) | 2005-09-01 |
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