KR20000076096A - 2-치환된 벤조일-사이클로알킬-1-카복실산 유도체 - Google Patents
2-치환된 벤조일-사이클로알킬-1-카복실산 유도체 Download PDFInfo
- Publication number
- KR20000076096A KR20000076096A KR1019997008184A KR19997008184A KR20000076096A KR 20000076096 A KR20000076096 A KR 20000076096A KR 1019997008184 A KR1019997008184 A KR 1019997008184A KR 19997008184 A KR19997008184 A KR 19997008184A KR 20000076096 A KR20000076096 A KR 20000076096A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- cyclopropane
- dichlorobenzoyl
- compound
- hydrogen
- Prior art date
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- -1 cyano, nitro, phenyl Chemical group 0.000 claims abstract description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 108010033242 Kynurenine 3-monooxygenase Proteins 0.000 claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 135
- 239000000203 mixture Substances 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 102100037652 Kynurenine 3-monooxygenase Human genes 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 208000030507 AIDS Diseases 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 229940125532 enzyme inhibitor Drugs 0.000 claims description 5
- 239000002532 enzyme inhibitor Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- JFJFPXNBPGWPNH-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)-3-methylcyclopropane-1-carboxylic acid Chemical compound CC1C(C(O)=O)C1C(=O)C1=CC=C(Cl)C(Cl)=C1 JFJFPXNBPGWPNH-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 229940122439 Hydroxylase inhibitor Drugs 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 230000002981 neuropathic effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- HJIVSCXTCIZJQA-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)-3-methylidenecyclopropane-1-carboxylic acid Chemical compound C=C1C(C(=O)O)C1C(=O)C1=CC=C(Cl)C(Cl)=C1 HJIVSCXTCIZJQA-UHFFFAOYSA-N 0.000 claims description 3
- LSYDATLNOABMJD-UHFFFAOYSA-N 3-(3,4-dichlorobenzoyl)-2,2-difluorocyclopropane-1-carboxylic acid Chemical compound FC1(F)C(C(=O)O)C1C(=O)C1=CC=C(Cl)C(Cl)=C1 LSYDATLNOABMJD-UHFFFAOYSA-N 0.000 claims description 3
- LZXZDLJRRHTOOA-UHFFFAOYSA-N 3-(3,4-dichlorobenzoyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(=O)C1=CC=C(Cl)C(Cl)=C1 LZXZDLJRRHTOOA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- YNEBLGHWBGZEHR-UHFFFAOYSA-N 1-amino-2-(3,4-dichlorobenzoyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(N)CC1C(=O)C1=CC=C(Cl)C(Cl)=C1 YNEBLGHWBGZEHR-UHFFFAOYSA-N 0.000 claims description 2
- YTTAYDFQLSNHHN-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)cyclobutane-1-carboxylic acid Chemical compound OC(=O)C1CCC1C(=O)C1=CC=C(Cl)C(Cl)=C1 YTTAYDFQLSNHHN-UHFFFAOYSA-N 0.000 claims description 2
- DNGSLZLFPSGCQH-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)cyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1C(=O)C1=CC=C(Cl)C(Cl)=C1 DNGSLZLFPSGCQH-UHFFFAOYSA-N 0.000 claims description 2
- SNVJBFKKUMRVTM-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)cyclopropane-1-carboxamide Chemical compound NC(=O)C1CC1C(=O)C1=CC=C(Cl)C(Cl)=C1 SNVJBFKKUMRVTM-UHFFFAOYSA-N 0.000 claims description 2
- ZBRKMOHDGFGXLN-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(=O)C1=CC=C(Cl)C(Cl)=C1 ZBRKMOHDGFGXLN-UHFFFAOYSA-N 0.000 claims description 2
- JBIPDCOYYLUUBX-UHFFFAOYSA-N 2-(3,4-difluorobenzoyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(=O)C1=CC=C(F)C(F)=C1 JBIPDCOYYLUUBX-UHFFFAOYSA-N 0.000 claims description 2
- DJRPLSCYUZAEQB-UHFFFAOYSA-N 2-(3-bromobenzoyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(=O)C1=CC=CC(Br)=C1 DJRPLSCYUZAEQB-UHFFFAOYSA-N 0.000 claims description 2
- QFHJDEIRMZKFIP-UHFFFAOYSA-N 2-(3-chlorobenzoyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(=O)C1=CC=CC(Cl)=C1 QFHJDEIRMZKFIP-UHFFFAOYSA-N 0.000 claims description 2
- UUMDEUZXEMIWBF-UHFFFAOYSA-N 2-(3-fluorobenzoyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(=O)C1=CC=CC(F)=C1 UUMDEUZXEMIWBF-UHFFFAOYSA-N 0.000 claims description 2
- 206010003694 Atrophy Diseases 0.000 claims description 2
- 208000002381 Brain Hypoxia Diseases 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- 206010019196 Head injury Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 206010061216 Infarction Diseases 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 230000037444 atrophy Effects 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 230000002518 glial effect Effects 0.000 claims description 2
- 230000007574 infarction Effects 0.000 claims description 2
- 230000000626 neurodegenerative effect Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 210000000278 spinal cord Anatomy 0.000 claims description 2
- 208000020431 spinal cord injury Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000003760 magnetic stirring Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 15
- 239000012267 brine Substances 0.000 description 14
- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 14
- YGPSJZOEDVAXAB-UHFFFAOYSA-N kynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- WJXSWCUQABXPFS-UHFFFAOYSA-N 3-hydroxyanthranilic acid Chemical compound NC1=C(O)C=CC=C1C(O)=O WJXSWCUQABXPFS-UHFFFAOYSA-N 0.000 description 5
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- 238000007796 conventional method Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- VCKPUUFAIGNJHC-UHFFFAOYSA-N 3-hydroxykynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(O)=C1N VCKPUUFAIGNJHC-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/18—Saturated compounds containing keto groups
- C07C62/20—Saturated compounds containing keto groups with a saturated six-membered ring
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than 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 singly-bound oxygen atoms
-
- 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
- C07C235/82—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 ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
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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
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/38—Unsaturated compounds containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9705031.4A GB9705031D0 (en) | 1997-03-11 | 1997-03-11 | 2-substituted benzoyl-cycloalkyl-1-carboxylic acid derivatives |
| GB9705031.4 | 1997-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000076096A true KR20000076096A (ko) | 2000-12-26 |
Family
ID=10809053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997008184A KR20000076096A (ko) | 1997-03-11 | 1998-02-16 | 2-치환된 벤조일-사이클로알킬-1-카복실산 유도체 |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0973720A1 (fr) |
| JP (1) | JP2001514634A (fr) |
| KR (1) | KR20000076096A (fr) |
| CN (1) | CN1252049A (fr) |
| AU (1) | AU6497998A (fr) |
| CA (1) | CA2283184A1 (fr) |
| EA (1) | EA199900809A1 (fr) |
| GB (1) | GB9705031D0 (fr) |
| HU (1) | HUP0001023A3 (fr) |
| IL (1) | IL131676A0 (fr) |
| NO (1) | NO994386L (fr) |
| PL (1) | PL335601A1 (fr) |
| TW (1) | TW407146B (fr) |
| WO (1) | WO1998040344A1 (fr) |
| ZA (1) | ZA981972B (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1424333A1 (fr) * | 2002-11-28 | 2004-06-02 | Newron Pharmaceuticals S.p.A. | Dérivés d'acide halothénoyl-cyclopropane-1-carboxylique |
| EP1475088A1 (fr) * | 2003-05-05 | 2004-11-10 | Newron Pharmaceuticals S.p.A. | Inhibiteurs de la kynurenine-3-hydroxylase pour le traitement des désordres locomoteurs induits par la L-DOPA, dyskinésies, accoutumance aux médicaments, douleurs et cataract |
| EP1475385A1 (fr) * | 2003-05-05 | 2004-11-10 | Newron Pharmaceuticals S.p.A. | Derivés de glycoside d'acide carboxylique de 2-(3,4-dichlorobenzoyl)-cyclopropane |
| SG11201406311UA (en) * | 2012-04-05 | 2014-11-27 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| CN103373911B (zh) * | 2012-04-27 | 2016-12-14 | 中国科学院上海有机化学研究所 | 单氟代环丙烷类化合物及其制备方法和应用 |
| CN104119246A (zh) * | 2013-04-26 | 2014-10-29 | 中国科学院上海有机化学研究所 | 环丙烷衍生物及其制备方法和应用 |
| JP2016536350A (ja) | 2013-09-26 | 2016-11-24 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | キヌレニン−３−モノオキシゲナーゼ阻害薬、医薬組成物、及びこれらの使用方法 |
| JP6449893B2 (ja) * | 2013-09-26 | 2019-01-09 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | キヌレニン−３−モノオキシゲナーゼ阻害薬、医薬組成物、及びこれらの使用方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655667A (en) * | 1968-04-04 | 1972-04-11 | Smith Kline French Lab | 1-(2-benzoylcyclopropylmethyl)-4-phenylpiperazines |
-
1997
- 1997-03-11 GB GBGB9705031.4A patent/GB9705031D0/en active Pending
-
1998
- 1998-02-16 EP EP98910685A patent/EP0973720A1/fr not_active Withdrawn
- 1998-02-16 EA EA199900809A patent/EA199900809A1/ru unknown
- 1998-02-16 HU HU0001023A patent/HUP0001023A3/hu unknown
- 1998-02-16 KR KR1019997008184A patent/KR20000076096A/ko not_active Application Discontinuation
- 1998-02-16 WO PCT/EP1998/000883 patent/WO1998040344A1/fr not_active Application Discontinuation
- 1998-02-16 CA CA002283184A patent/CA2283184A1/fr not_active Abandoned
- 1998-02-16 PL PL98335601A patent/PL335601A1/xx unknown
- 1998-02-16 IL IL13167698A patent/IL131676A0/xx unknown
- 1998-02-16 CN CN98804144A patent/CN1252049A/zh active Pending
- 1998-02-16 JP JP53912398A patent/JP2001514634A/ja not_active Withdrawn
- 1998-02-16 AU AU64979/98A patent/AU6497998A/en not_active Abandoned
- 1998-02-26 TW TW087102847A patent/TW407146B/zh active
- 1998-03-09 ZA ZA981972A patent/ZA981972B/xx unknown
-
1999
- 1999-09-10 NO NO994386A patent/NO994386L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO994386D0 (no) | 1999-09-10 |
| HUP0001023A3 (en) | 2001-03-28 |
| EA199900809A1 (ru) | 2000-08-28 |
| EP0973720A1 (fr) | 2000-01-26 |
| HUP0001023A2 (hu) | 2000-09-28 |
| IL131676A0 (en) | 2001-03-19 |
| WO1998040344A1 (fr) | 1998-09-17 |
| TW407146B (en) | 2000-10-01 |
| NO994386L (no) | 1999-11-02 |
| GB9705031D0 (en) | 1997-04-30 |
| JP2001514634A (ja) | 2001-09-11 |
| CA2283184A1 (fr) | 1998-09-17 |
| AU6497998A (en) | 1998-09-29 |
| PL335601A1 (en) | 2000-05-08 |
| ZA981972B (en) | 1998-09-09 |
| CN1252049A (zh) | 2000-05-03 |
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| Date | Code | Title | Description |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |