ZA200205706B - Dehydroamino acids. - Google Patents
Dehydroamino acids. Download PDFInfo
- Publication number
- ZA200205706B ZA200205706B ZA200205706A ZA200205706A ZA200205706B ZA 200205706 B ZA200205706 B ZA 200205706B ZA 200205706 A ZA200205706 A ZA 200205706A ZA 200205706 A ZA200205706 A ZA 200205706A ZA 200205706 B ZA200205706 B ZA 200205706B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- hydrogen
- compound
- halogen
- lower alkyl
- Prior art date
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- 239000002253 acid Substances 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 83
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- -1 hydroxy, amino Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 230000006044 T cell activation Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 55
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 36
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 21
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 4
- 102100025390 Integrin beta-2 Human genes 0.000 description 4
- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 3
- 108091008874 T cell receptors Proteins 0.000 description 2
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
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- ZCSFJHGBYFIMMH-MYYYXRDXSA-N (z)-2-[[2-bromo-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-naphthalen-1-ylprop-2-enoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1/C=C(C(=O)O)\NC(=O)C(C(=C1)Br)=CC=C1C(=O)NCC1=CC=CC(O)=C1 ZCSFJHGBYFIMMH-MYYYXRDXSA-N 0.000 description 1
- YVAPRXDUAPMMAJ-NDENLUEZSA-N (z)-2-[[2-bromo-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-pyridin-2-ylprop-2-enoic acid Chemical compound C=1C=CC=NC=1/C=C(C(=O)O)\NC(=O)C(C(=C1)Br)=CC=C1C(=O)NCC1=CC=CC(O)=C1 YVAPRXDUAPMMAJ-NDENLUEZSA-N 0.000 description 1
- NJOFVFQIGWZHOG-OCKHKDLRSA-N (z)-2-[[2-bromo-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-thiophen-3-ylprop-2-enoic acid Chemical compound C1=CSC=C1/C=C(C(=O)O)\NC(=O)C(C(=C1)Br)=CC=C1C(=O)NCC1=CC=CC(O)=C1 NJOFVFQIGWZHOG-OCKHKDLRSA-N 0.000 description 1
- DGARIVJPAYJFOP-MTJSOVHGSA-N (z)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]-6-methylbenzoyl]amino]-3-phenylprop-2-enoic acid Chemical compound CC1=CC(C(=O)NCC=2C=C(O)C=CC=2)=CC(Cl)=C1C(=O)N\C(C(O)=O)=C/C1=CC=CC=C1 DGARIVJPAYJFOP-MTJSOVHGSA-N 0.000 description 1
- BSEDNGNCYROORI-MSXFZWOLSA-N (z)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]-6-methylbenzoyl]amino]-3-quinolin-3-ylprop-2-enoic acid Chemical compound C=1C(Cl)=C(C(=O)N\C(=C/C=2C=C3C=CC=CC3=NC=2)C(O)=O)C(C)=CC=1C(=O)NCC1=CC=CC(O)=C1 BSEDNGNCYROORI-MSXFZWOLSA-N 0.000 description 1
- NEQKNAIRISOSEH-JAIQZWGSSA-N (z)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-(4-methyl-2-propan-2-yl-1,3-thiazol-5-yl)prop-2-enoic acid Chemical compound S1C(C(C)C)=NC(C)=C1\C=C(C(O)=O)/NC(=O)C1=CC=C(C(=O)NCC=2C=C(O)C=CC=2)C=C1Cl NEQKNAIRISOSEH-JAIQZWGSSA-N 0.000 description 1
- CFEDBPRPZARLBA-GRSHGNNSSA-N (z)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-(4-propan-2-yl-1,3-thiazol-5-yl)prop-2-enoic acid Chemical compound N1=CSC(\C=C(/NC(=O)C=2C(=CC(=CC=2)C(=O)NCC=2C=C(O)C=CC=2)Cl)C(O)=O)=C1C(C)C CFEDBPRPZARLBA-GRSHGNNSSA-N 0.000 description 1
- NEFCDEHZKVKMMO-NHDPSOOVSA-N (z)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-(4-sulfamoylphenyl)prop-2-enoic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1\C=C(C(O)=O)/NC(=O)C1=CC=C(C(=O)NCC=2C=C(O)C=CC=2)C=C1Cl NEFCDEHZKVKMMO-NHDPSOOVSA-N 0.000 description 1
- KBHWTNIGYHFQGU-SXGWCWSVSA-N (z)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]-3-[2-(methylamino)-4-(trifluoromethyl)-1,3-thiazol-5-yl]prop-2-enoic acid Chemical compound S1C(NC)=NC(C(F)(F)F)=C1\C=C(C(O)=O)/NC(=O)C1=CC=C(C(=O)NCC=2C=C(O)C=CC=2)C=C1Cl KBHWTNIGYHFQGU-SXGWCWSVSA-N 0.000 description 1
- DNKVMXXWVSZGFH-OYKKKHCWSA-N (z)-2-[[4-[(3-hydroxyphenyl)methylcarbamoyl]-2-methylbenzoyl]amino]-3-(1h-indol-6-yl)prop-2-enoic acid Chemical compound C=1C=C(C(=O)N\C(=C/C=2C=C3NC=CC3=CC=2)C(O)=O)C(C)=CC=1C(=O)NCC1=CC=CC(O)=C1 DNKVMXXWVSZGFH-OYKKKHCWSA-N 0.000 description 1
- UZPAYZPHRHQEKR-HMAPJEAMSA-N (z)-2-[[4-[(3-hydroxyphenyl)methylcarbamoyl]-2-methylbenzoyl]amino]-3-phenylprop-2-enoic acid Chemical compound CC1=CC(C(=O)NCC=2C=C(O)C=CC=2)=CC=C1C(=O)N\C(C(O)=O)=C/C1=CC=CC=C1 UZPAYZPHRHQEKR-HMAPJEAMSA-N 0.000 description 1
- DQCJMRMVVKPEIT-UUYOSTAYSA-N (z)-3-(1-benzothiophen-3-yl)-2-[[2-bromo-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]prop-2-enoic acid Chemical compound C=1SC2=CC=CC=C2C=1/C=C(C(=O)O)\NC(=O)C(C(=C1)Br)=CC=C1C(=O)NCC1=CC=CC(O)=C1 DQCJMRMVVKPEIT-UUYOSTAYSA-N 0.000 description 1
- DZEVJKNTHOCVPX-FBHDLOMBSA-N (z)-3-(2,1,3-benzothiadiazol-5-yl)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]prop-2-enoic acid Chemical compound C1=CC2=NSN=C2C=C1/C=C(C(=O)O)\NC(=O)C(C(=C1)Cl)=CC=C1C(=O)NCC1=CC=CC(O)=C1 DZEVJKNTHOCVPX-FBHDLOMBSA-N 0.000 description 1
- VXSYCMORWJFQNP-FBHDLOMBSA-N (z)-3-(2h-benzotriazol-5-yl)-2-[[2-bromo-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]prop-2-enoic acid Chemical compound C=1C=C2NN=NC2=CC=1/C=C(C(=O)O)\NC(=O)C(C(=C1)Br)=CC=C1C(=O)NCC1=CC=CC(O)=C1 VXSYCMORWJFQNP-FBHDLOMBSA-N 0.000 description 1
- BPOMJZAKTRTFRI-NHDPSOOVSA-N (z)-3-(4-bromophenyl)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]prop-2-enoic acid Chemical compound C=1C=C(Br)C=CC=1/C=C(C(=O)O)\NC(=O)C(C(=C1)Cl)=CC=C1C(=O)NCC1=CC=CC(O)=C1 BPOMJZAKTRTFRI-NHDPSOOVSA-N 0.000 description 1
- HPSMZJCCJTWZRA-UHFFFAOYSA-N 2-[[2-bromo-4-[(3-hydroxyphenyl)methylcarbamoyl]benzoyl]amino]prop-2-enoic acid Chemical compound C1=C(Br)C(C(=O)NC(=C)C(=O)O)=CC=C1C(=O)NCC1=CC=CC(O)=C1 HPSMZJCCJTWZRA-UHFFFAOYSA-N 0.000 description 1
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- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 description 1
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- 102100037877 Intercellular adhesion molecule 1 Human genes 0.000 description 1
- 102100037872 Intercellular adhesion molecule 2 Human genes 0.000 description 1
- 101710148794 Intercellular adhesion molecule 2 Proteins 0.000 description 1
- 102100037871 Intercellular adhesion molecule 3 Human genes 0.000 description 1
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- 230000004913 activation Effects 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
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- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
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- 230000028709 inflammatory response Effects 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000023404 leukocyte cell-cell adhesion Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/85—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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US6331640B1 (en) * | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
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BR0305426A (pt) * | 2002-07-01 | 2004-08-24 | Upjohn Co | Compostos inibidores de ns5b polimerase de hcv, bem como composição farmacêutica compreendendo os mesmos |
AU2003282510A1 (en) | 2002-10-11 | 2004-05-04 | Bristol-Myers Squibb Company | Hexahydro-benzimidazolone compounds useful as anti-inflammatory agents |
ES2383525T3 (es) * | 2003-11-05 | 2012-06-21 | Sarcode Bioscience Inc. | Moduladores de la adhesión celular |
JP2007535553A (ja) * | 2004-04-29 | 2007-12-06 | アボット・ラボラトリーズ | アミノ−テトラゾール類縁体および使用方法 |
AU2005286793A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes |
TW200616634A (en) | 2004-10-01 | 2006-06-01 | Bristol Myers Squibb Co | Crystalline forms and process for preparing spiro-hydantoin compounds |
US7186727B2 (en) | 2004-12-14 | 2007-03-06 | Bristol-Myers Squibb Company | Pyridyl-substituted spiro-hydantoin compounds and use thereof |
CA2609053C (fr) | 2005-05-17 | 2017-04-25 | Sarcode Corporation | Compositions et procedes pour le traitement des troubles oculaires |
EP3797775A1 (fr) | 2007-10-19 | 2021-03-31 | Novartis AG | Compositions et procédés pour le traitement de la rétinopathie diabétique |
JP2011518155A (ja) * | 2008-04-15 | 2011-06-23 | サーコード コーポレイション | 免疫関連障害の局所治療に使用するためのエアゾール化lfa−1アンタゴニスト |
ES2763703T3 (es) * | 2008-04-15 | 2020-05-29 | Sarcode Bioscience Inc | Antagonistas de LFA-1 tópicos utilizados en el tratamiento localizado de trastornos inmunes |
WO2009139817A2 (fr) | 2008-04-15 | 2009-11-19 | Sarcode Corporation | Produit pharmaceutique cristallin et ses procédés de préparation et d'utilisation |
CN102065893A (zh) * | 2008-04-15 | 2011-05-18 | 萨可德公司 | Lfa-1拮抗剂向胃肠系统的递送 |
US8378105B2 (en) * | 2009-10-21 | 2013-02-19 | Sarcode Bioscience Inc. | Crystalline pharmaceutical and methods of preparation and use thereof |
US20120270875A1 (en) * | 2011-03-16 | 2012-10-25 | Paul Gillespie | Pyrimidine amide compounds |
KR20140121453A (ko) | 2012-01-27 | 2014-10-15 | 에프. 호프만-라 로슈 아게 | Lfa-1 발현 세포로의 표적화 전달을 위한 인테그린 안타고니스트 |
MX2015001098A (es) | 2012-07-25 | 2015-09-25 | Sarcode Bioscience Inc | Inhibidor del antigeno-1 asociado a la funcion del linfocito (lfa-1) y polimorfo del mismo. |
CN106631867B (zh) * | 2016-12-27 | 2018-06-22 | 河南省科学院化学研究所有限公司 | 一种合成2-苯甲酰氨基-3-芳基丙烯酸酯的方法 |
CN116334049B (zh) * | 2019-11-20 | 2023-11-17 | 珠海联邦制药股份有限公司 | 人工设计的赖氨酰内切酶及编码序列和发酵方法 |
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US3984428A (en) | 1968-11-22 | 1976-10-05 | Hoffmann-La Roche Inc. | Isoxazolyl-substituted perhydrobenzindenes |
US5369106A (en) | 1989-04-28 | 1994-11-29 | Sankyo Company, Limited | N-acryloylpiperazine derivatives, their preparation and their use of PAF antagonists |
US4992468A (en) | 1989-07-26 | 1991-02-12 | Allergan, Inc. | Phenylethenyl compounds having retinoid-like activity |
US5457124A (en) | 1993-12-07 | 1995-10-10 | Hoffmann-La Roche Inc. | Carboxylic acid Leukotriene B4 antagonists |
JPH10175970A (ja) * | 1996-12-19 | 1998-06-30 | Mitsui Chem Inc | ベンゾチオフェン誘導体およびそれを有効成分として含有する医薬品 |
KR100596109B1 (ko) | 1998-03-27 | 2006-07-05 | 제넨테크, 인크. | Cd11/cd18 부착 수용체 매개 질환 치료용 길항제 |
JP2000072766A (ja) * | 1998-08-27 | 2000-03-07 | Dai Ichi Seiyaku Co Ltd | ベンゾピラン誘導体 |
WO2000015604A1 (fr) * | 1998-09-11 | 2000-03-23 | Kyorin Pharmaceutical Co., Ltd. | Derives de diesters maloniques et leur procede d'obtention |
US6331640B1 (en) | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
CN1351588A (zh) * | 1999-04-02 | 2002-05-29 | 伊科斯公司 | 白细胞功能相关抗原与细胞间粘着分子结合的抑制剂及其用途 |
EP1046651A1 (fr) * | 1999-04-19 | 2000-10-25 | Koninklijke Universiteit Nijmegen | Composition et méthode pour moduler l'interaction des cellules dendritiques et les cellules T |
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- 2001-02-01 JP JP2001558405A patent/JP2003522751A/ja active Pending
- 2001-02-01 CA CA002397993A patent/CA2397993A1/fr not_active Abandoned
- 2001-02-01 AU AU3022701A patent/AU3022701A/xx active Pending
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AU2001230227B2 (en) | 2006-03-16 |
EP1261579A1 (fr) | 2002-12-04 |
KR20020073206A (ko) | 2002-09-19 |
CA2397993A1 (fr) | 2001-08-16 |
US6515124B2 (en) | 2003-02-04 |
WO2001058853A1 (fr) | 2001-08-16 |
MXPA02007461A (es) | 2002-12-13 |
BR0108240A (pt) | 2002-10-29 |
CN1257886C (zh) | 2006-05-31 |
AU3022701A (en) | 2001-08-20 |
CN1398252A (zh) | 2003-02-19 |
KR100710958B1 (ko) | 2007-04-24 |
JP2003522751A (ja) | 2003-07-29 |
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