ZA200605248B - Cyclopropane compounds and pharmaceutical use thereof - Google Patents
Cyclopropane compounds and pharmaceutical use thereof Download PDFInfo
- Publication number
- ZA200605248B ZA200605248B ZA200605248A ZA200605248A ZA200605248B ZA 200605248 B ZA200605248 B ZA 200605248B ZA 200605248 A ZA200605248 A ZA 200605248A ZA 200605248 A ZA200605248 A ZA 200605248A ZA 200605248 B ZA200605248 B ZA 200605248B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- sulfonylamino
- cyclopropanecarboxylic acid
- thiophene
- chloro
- Prior art date
Links
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 title claims description 11
- -1 cyclopropane compound Chemical class 0.000 claims description 183
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 65
- GBLRQXKSCRCLBZ-AJSYEDJNSA-N (1S,2R,1'S,2'R)-doxacurium Chemical compound COC1=C(OC)C(OC)=CC(C[C@@H]2[N@@+](CCC3=C2C(=C(OC)C(OC)=C3)OC)(C)CCCOC(=O)CCC(=O)OCCC[N@+]2(C)[C@H](C3=C(OC)C(OC)=C(OC)C=C3CC2)CC=2C=C(OC)C(OC)=C(OC)C=2)=C1 GBLRQXKSCRCLBZ-AJSYEDJNSA-N 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 150000002430 hydrocarbons Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229940124597 therapeutic agent Drugs 0.000 claims description 23
- 125000005647 linker group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 17
- 201000008482 osteoarthritis Diseases 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 15
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 13
- FNFJZXAWCAEGNI-UHFFFAOYSA-N cycloheptene-1-carboxylic acid Chemical compound OC(=O)C1=CCCCCC1 FNFJZXAWCAEGNI-UHFFFAOYSA-N 0.000 claims description 11
- 230000000069 prophylactic effect Effects 0.000 claims description 11
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 7
- 229940124761 MMP inhibitor Drugs 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 102100027995 Collagenase 3 Human genes 0.000 claims description 5
- 108050005238 Collagenase 3 Proteins 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 229940123879 Aggrecanase inhibitor Drugs 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- IWWCCNVRNHTGLV-UHFFFAOYSA-N 1-phenylcyclopropane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CC1 IWWCCNVRNHTGLV-UHFFFAOYSA-N 0.000 claims description 3
- AHDDRJBFJBDEPW-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1=CC=CC=C1 AHDDRJBFJBDEPW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- DLGXTIVBQACKAB-KUHUBIRLSA-N (1s,2r)-1-[[5-(5-methylthiophen-2-yl)thiophen-2-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound S1C(C)=CC=C1C1=CC=C(S(=O)(=O)N[C@@]2([C@H](C2)C=2C=CC=CC=2)C(O)=O)S1 DLGXTIVBQACKAB-KUHUBIRLSA-N 0.000 claims description 2
- GMLPMVRJEJKCGE-DIFFPNOSSA-N (1s,2r)-2-phenyl-1-[[5-[4-(trifluoromethyl)-1,3-thiazol-2-yl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound C1([C@H]2C[C@]2(C(=O)O)NS(=O)(=O)C=2SC(=CC=2)C=2SC=C(N=2)C(F)(F)F)=CC=CC=C1 GMLPMVRJEJKCGE-DIFFPNOSSA-N 0.000 claims description 2
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 5
- 239000005711 Benzoic acid Substances 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 3
- 241001481828 Glyptocephalus cynoglossus Species 0.000 claims 3
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 2
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- JRZGPWOEHDOVMC-UHFFFAOYSA-N n-hydroxynaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NO)=CC=CC2=C1 JRZGPWOEHDOVMC-UHFFFAOYSA-N 0.000 claims 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 claims 1
- INWDSKYBLLDZEB-MGPUTAFESA-N (1r,2s)-2-(2-bromophenyl)-1-[[5-(4-chlorophenyl)thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound C1([C@@H]2C[C@@]2(C(=O)O)NS(=O)(=O)C=2SC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=CC=C1Br INWDSKYBLLDZEB-MGPUTAFESA-N 0.000 claims 1
- GGDFKGNDCXEPDV-VWNXMTODSA-N (1s,2r)-1-[(2-cyclohexyl-1,3-dihydroisoindol-5-yl)sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1([C@H]2C[C@]2(C(=O)O)NS(=O)(=O)C=2C=C3CN(CC3=CC=2)C2CCCCC2)=CC=CC=C1 GGDFKGNDCXEPDV-VWNXMTODSA-N 0.000 claims 1
- KRLBUZMEHUUWOC-APWZRJJASA-N (1s,2r)-1-[(5-pent-1-ynylthiophen-2-yl)sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound S1C(C#CCCC)=CC=C1S(=O)(=O)N[C@]1(C(O)=O)[C@@H](C=2C=CC=CC=2)C1 KRLBUZMEHUUWOC-APWZRJJASA-N 0.000 claims 1
- YSQZHNXCWCNDJY-XLIONFOSSA-N (1s,2r)-1-[2-(1-benzofuran-2-yl)ethylsulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1([C@H]2C[C@]2(C(=O)O)NS(=O)(=O)CCC=2OC3=CC=CC=C3C=2)=CC=CC=C1 YSQZHNXCWCNDJY-XLIONFOSSA-N 0.000 claims 1
- WLIRTYLMHWZDJW-APWZRJJASA-N (1s,2r)-1-[[4-(3-methylbutanoyl)piperazin-1-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1CN(C(=O)CC(C)C)CCN1S(=O)(=O)N[C@]1(C(O)=O)[C@@H](C=2C=CC=CC=2)C1 WLIRTYLMHWZDJW-APWZRJJASA-N 0.000 claims 1
- GRLDJRIUBKFBOF-MJGOQNOKSA-N (1s,2r)-1-[[4-(3-methylbutyl)piperazin-1-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1CN(CCC(C)C)CCN1S(=O)(=O)N[C@]1(C(O)=O)[C@@H](C=2C=CC=CC=2)C1 GRLDJRIUBKFBOF-MJGOQNOKSA-N 0.000 claims 1
- WMYQMNFSIVBXIY-PBHICJAKSA-N (1s,2r)-1-[[4-(ethylcarbamoyl)piperazin-1-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1CN(C(=O)NCC)CCN1S(=O)(=O)N[C@]1(C(O)=O)[C@@H](C=2C=CC=CC=2)C1 WMYQMNFSIVBXIY-PBHICJAKSA-N 0.000 claims 1
- LPYJXZHJKUXMPT-DHIUTWEWSA-N (1s,2r)-1-[[5-(2,3-dihydro-1,4-benzodioxin-6-yl)thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1([C@@]2([C@](C2)(NS(=O)(=O)C=2SC(=CC=2)C=2C=C3OCCOC3=CC=2)C(O)=O)C)=CC=CC=C1 LPYJXZHJKUXMPT-DHIUTWEWSA-N 0.000 claims 1
- IDTWZMNMPDGNTI-IEBWSBKVSA-N (1s,2r)-1-[[5-(3,3-difluoropyrrolidin-1-yl)thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1N1CCC(F)(F)C1 IDTWZMNMPDGNTI-IEBWSBKVSA-N 0.000 claims 1
- ZBXRDIOAQNVNGQ-WOJBJXKFSA-N (1s,2r)-1-[[5-(3,5-difluoropyridin-2-yl)thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=NC=C(F)C=C1F ZBXRDIOAQNVNGQ-WOJBJXKFSA-N 0.000 claims 1
- XMIVZHZOMHJNOT-NHCUHLMSSA-N (1s,2r)-1-[[5-(3-chloro-4-fluorophenyl)thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=CC=C(F)C(Cl)=C1 XMIVZHZOMHJNOT-NHCUHLMSSA-N 0.000 claims 1
- PWZJQJMPTKKOPX-UTKZUKDTSA-N (1s,2r)-1-[[5-(4-chlorophenyl)thiophen-2-yl]sulfonylamino]-2-[2-(hydroxymethyl)phenyl]cyclopropane-1-carboxylic acid Chemical compound OCC1=CC=CC=C1[C@@H]1[C@@](C(O)=O)(NS(=O)(=O)C=2SC(=CC=2)C=2C=CC(Cl)=CC=2)C1 PWZJQJMPTKKOPX-UTKZUKDTSA-N 0.000 claims 1
- LXKHVQYMYLBFCC-UZLBHIALSA-N (1s,2r)-1-[[5-(4-chlorophenyl)thiophen-2-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1([C@H]2C[C@]2(C(=O)O)NS(=O)(=O)C=2SC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=CC=C1 LXKHVQYMYLBFCC-UZLBHIALSA-N 0.000 claims 1
- PJELZTVMJWQSTJ-FGZHOGPDSA-N (1s,2r)-1-[[5-(4-cyano-3-fluorophenyl)thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=CC=C(C#N)C(F)=C1 PJELZTVMJWQSTJ-FGZHOGPDSA-N 0.000 claims 1
- FLNYZVZXGFJGPF-NHCUHLMSSA-N (1s,2r)-1-[[5-(4-hydroxyphenyl)thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=CC=C(O)C=C1 FLNYZVZXGFJGPF-NHCUHLMSSA-N 0.000 claims 1
- SLYNKAWTTGTVCE-UZLBHIALSA-N (1s,2r)-1-[[5-(4-methylpiperidin-1-yl)thiophen-2-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1CC(C)CCN1C1=CC=C(S(=O)(=O)N[C@@]2([C@H](C2)C=2C=CC=CC=2)C(O)=O)S1 SLYNKAWTTGTVCE-UZLBHIALSA-N 0.000 claims 1
- RIAYQBVTVQKYTD-ACJLOTCBSA-N (1s,2r)-1-[[5-(5-methyl-1,3-thiazol-2-yl)thiophen-2-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound S1C(C)=CN=C1C1=CC=C(S(=O)(=O)N[C@@]2([C@H](C2)C=2C=CC=CC=2)C(O)=O)S1 RIAYQBVTVQKYTD-ACJLOTCBSA-N 0.000 claims 1
- CPPNUMROHJEKLG-FGZHOGPDSA-N (1s,2r)-1-[[5-[3-(1,1-difluoro-2-hydroxyethyl)phenyl]thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=CC=CC(C(F)(F)CO)=C1 CPPNUMROHJEKLG-FGZHOGPDSA-N 0.000 claims 1
- XJARQXLFUIOSSQ-DNQXCXABSA-N (1s,2r)-1-[[5-[3-(3-hydroxypropoxy)phenyl]thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=CC=CC(OCCCO)=C1 XJARQXLFUIOSSQ-DNQXCXABSA-N 0.000 claims 1
- PQTUYKMPBUFIAG-DHIUTWEWSA-N (1s,2r)-1-[[5-[3-(hydroxymethyl)-4-methoxyphenyl]thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1=C(CO)C(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@@]2([C@@](C2)(C)C=2C=CC=CC=2)C(O)=O)S1 PQTUYKMPBUFIAG-DHIUTWEWSA-N 0.000 claims 1
- RRTUDIKKZHXASW-DHIUTWEWSA-N (1s,2r)-1-[[5-[4-chloro-3-(dimethylamino)phenyl]thiophen-2-yl]sulfonylamino]-2-methyl-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1=C(Cl)C(N(C)C)=CC(C=2SC(=CC=2)S(=O)(=O)N[C@@]2([C@@](C2)(C)C=2C=CC=CC=2)C(O)=O)=C1 RRTUDIKKZHXASW-DHIUTWEWSA-N 0.000 claims 1
- ZXGVHXUTEHUGFU-APWZRJJASA-N (1s,2r)-1-[[6-(4-methylpyrazol-1-yl)pyridin-3-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1=C(C)C=NN1C1=CC=C(S(=O)(=O)N[C@@]2([C@H](C2)C=2C=CC=CC=2)C(O)=O)C=N1 ZXGVHXUTEHUGFU-APWZRJJASA-N 0.000 claims 1
- MTFYFNMACVCXEN-QZTJIDSGSA-N (1s,2r)-2-(3-fluorophenyl)-2-methyl-1-[[5-[5-(trifluoromethyl)-1,2-oxazol-3-yl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=C(F)C=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C=1C=C(C(F)(F)F)ON=1 MTFYFNMACVCXEN-QZTJIDSGSA-N 0.000 claims 1
- LPJNZESZIMXILB-RTBURBONSA-N (1s,2r)-2-(3-methoxyphenyl)-2-methyl-1-[[5-[5-(trifluoromethyl)-1,2-oxazol-3-yl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound COC1=CC=CC([C@]2(C)[C@](C2)(NS(=O)(=O)C=2SC(=CC=2)C2=NOC(=C2)C(F)(F)F)C(O)=O)=C1 LPJNZESZIMXILB-RTBURBONSA-N 0.000 claims 1
- BFKPRDLOLDWWJU-FGZHOGPDSA-N (1s,2r)-2-methyl-1-[[5-(n-methylanilino)thiophen-2-yl]sulfonylamino]-2-phenylcyclopropane-1-carboxylic acid Chemical compound C1([C@@]2(C)C[C@@]2(NS(=O)(=O)C2=CC=C(S2)N(C)C=2C=CC=CC=2)C(O)=O)=CC=CC=C1 BFKPRDLOLDWWJU-FGZHOGPDSA-N 0.000 claims 1
- NPVPGRQHNPOUIB-VEUZHWNKSA-N (1s,2r)-2-methyl-2-phenyl-1-[[5-[(e)-3,3,3-trifluoroprop-1-enyl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C1=CC=C(\C=C\C(F)(F)F)S1 NPVPGRQHNPOUIB-VEUZHWNKSA-N 0.000 claims 1
- NPVPGRQHNPOUIB-CZDHMLMNSA-N (1s,2r)-2-methyl-2-phenyl-1-[[5-[(z)-3,3,3-trifluoroprop-1-enyl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C1=CC=C(\C=C/C(F)(F)F)S1 NPVPGRQHNPOUIB-CZDHMLMNSA-N 0.000 claims 1
- HGZMGHJHBPJQRW-NHCUHLMSSA-N (1s,2r)-2-methyl-2-phenyl-1-[[5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 HGZMGHJHBPJQRW-NHCUHLMSSA-N 0.000 claims 1
- BYTZDMOXWOLBAF-QZTJIDSGSA-N (1s,2r)-2-methyl-2-phenyl-1-[[5-[4-(trifluoromethyl)pyrazol-1-yl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1N1C=C(C(F)(F)F)C=N1 BYTZDMOXWOLBAF-QZTJIDSGSA-N 0.000 claims 1
- RGRZNINNTKZSTE-QZTJIDSGSA-N (1s,2r)-2-methyl-2-phenyl-1-[[5-[5-(trifluoromethyl)-1,2-oxazol-3-yl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound N([C@]1(C[C@]1(C)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(S1)=CC=C1C=1C=C(C(F)(F)F)ON=1 RGRZNINNTKZSTE-QZTJIDSGSA-N 0.000 claims 1
- VGEPKHWFWXRDSO-MJGOQNOKSA-N (1s,2r)-2-phenyl-1-[(1-phenylpyrazol-4-yl)sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound C1([C@H]2C[C@]2(C(=O)O)NS(=O)(=O)C2=CN(N=C2)C=2C=CC=CC=2)=CC=CC=C1 VGEPKHWFWXRDSO-MJGOQNOKSA-N 0.000 claims 1
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- NMUWWUKUOAYQQI-JGFGOQIWSA-N (1s,2r,3r)-1-[(5-ethynylthiophen-2-yl)sulfonylamino]-2-methyl-3-phenylcyclopropane-1-carboxylic acid Chemical compound C1([C@H]2[C@H]([C@@]2(NS(=O)(=O)C=2SC(=CC=2)C#C)C(O)=O)C)=CC=CC=C1 NMUWWUKUOAYQQI-JGFGOQIWSA-N 0.000 claims 1
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- NSOFPHHZFFCCOT-ONUMYQOESA-N (1s,2r,3r)-2-methyl-3-phenyl-1-[[5-[3-(trifluoromethyl)pyrazol-1-yl]thiophen-2-yl]sulfonylamino]cyclopropane-1-carboxylic acid Chemical compound C1([C@H]2[C@H]([C@@]2(NS(=O)(=O)C=2SC(=CC=2)N2N=C(C=C2)C(F)(F)F)C(O)=O)C)=CC=CC=C1 NSOFPHHZFFCCOT-ONUMYQOESA-N 0.000 claims 1
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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- C—CHEMISTRY; METALLURGY
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- 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
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the 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
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- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide 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
- 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
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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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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- C07C2603/08—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing three- or four-membered rings
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- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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- C—CHEMISTRY; METALLURGY
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
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EP (1) | EP1694410B1 (ru) |
JP (1) | JP2007516982A (ru) |
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RU (1) | RU2006125441A (ru) |
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JP2007516981A (ja) * | 2003-12-15 | 2007-06-28 | 日本たばこ産業株式会社 | N−置換−n−スルホニルアミノシクロプロパン化合物及びその医薬用途 |
JP2008530162A (ja) * | 2005-02-15 | 2008-08-07 | グラクソ グループ リミテッド | グルタミン酸受容体を増強する化合物および医薬におけるそれらの使用 |
CA2618360C (en) | 2005-08-04 | 2015-06-09 | Sirtris Pharmaceuticals, Inc. | Benzothiazoles and thiazolopyridines as sirtuin modulators |
WO2008147763A1 (en) * | 2007-05-23 | 2008-12-04 | Array Biopharma Inc. | Mmp inhibitors and methods of use thereof |
TW200918542A (en) | 2007-06-20 | 2009-05-01 | Sirtris Pharmaceuticals Inc | Sirtuin modulating compounds |
NZ584100A (en) | 2007-08-22 | 2011-07-29 | Astrazeneca Ab | Cyclopropyl amide derivatives |
WO2009094224A1 (en) * | 2008-01-25 | 2009-07-30 | Millennium Pharmaceuticals, Inc. | Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
RU2490272C2 (ru) * | 2008-02-04 | 2013-08-20 | Айденикс Фармасьютикалз, Инк. | Макроциклические ингибиторы серинпротеазы |
US9602777B2 (en) | 2008-04-25 | 2017-03-21 | Roche Diagnostics Hematology, Inc. | Systems and methods for analyzing body fluids |
KR101682427B1 (ko) | 2008-12-23 | 2016-12-05 | 아쿠일루스 파마슈티컬즈, 인코포레이티드 | 통증 및 기타 질병을 치료하기 위한 화합물 및 방법 |
EP2389362B1 (en) | 2009-01-21 | 2019-12-11 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
TW201039825A (en) * | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
US8377962B2 (en) | 2009-04-08 | 2013-02-19 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors |
WO2010141680A2 (en) * | 2009-06-03 | 2010-12-09 | The Board Of Trustees The Leland Stanford Junior University | Hedgehog pathway antagonists and methods of use |
US9284307B2 (en) | 2009-08-05 | 2016-03-15 | Idenix Pharmaceuticals Llc | Macrocyclic serine protease inhibitors |
AU2010297557C1 (en) | 2009-09-25 | 2017-04-06 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
US8530453B2 (en) * | 2009-09-28 | 2013-09-10 | Aquilus Pharmaceuticals, Inc. | Compounds and methods for the treatment of pain and other diseases |
US8946296B2 (en) | 2009-10-09 | 2015-02-03 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl-cyclopropylamine acetamides and their use |
TWI520945B (zh) | 2010-02-18 | 2016-02-11 | 阿斯特捷利康公司 | 環丙基苯甲醯胺衍生物之新穎結晶形式 |
WO2011106574A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
US9186337B2 (en) | 2010-02-24 | 2015-11-17 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for diseases and disorders associated with Hepadnaviridae |
BR122019020471B1 (pt) | 2010-04-19 | 2021-06-22 | Oryzon Genomics S.A. | Inibidores da desmetilase específica para lisina 1, seus usos e método para sua identificação, e composições farmacêuticas |
HUE037937T2 (hu) | 2010-07-29 | 2021-11-29 | Oryzon Genomics Sa | Arilciklopropilamin-alapú LSD1-demetiláz inhibitorok és gyógyászati alkalmazásuk |
US9006449B2 (en) | 2010-07-29 | 2015-04-14 | Oryzon Genomics, S.A. | Cyclopropylamine derivatives useful as LSD1 inhibitors |
US9061966B2 (en) | 2010-10-08 | 2015-06-23 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
HU1000676D0 (en) | 2010-12-17 | 2011-02-28 | Pharmahungary 2000 Kft | Inhibitors of matrix metalloproteinase, pharmaceutical compositions thereof and use of them for preventing and treating diseases where the activation of mmp is involved |
WO2012107498A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
US9353100B2 (en) | 2011-02-10 | 2016-05-31 | Idenix Pharmaceuticals Llc | Macrocyclic serine protease inhibitors, pharmaceutical compositions thereof, and their use for treating HCV infections |
BR112014009306B1 (pt) | 2011-10-20 | 2021-07-20 | Oryzon Genomics S.A. | Compostos de (hetero)aril ciclopropilamina como inibidores de lsd1 |
SG11201401066PA (en) | 2011-10-20 | 2014-10-30 | Oryzon Genomics Sa | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
EP2953932B1 (en) | 2013-02-06 | 2017-03-01 | Merck Patent GmbH | Substituted carboxylic acid derivatives as aggrecanase inhibitors for the treatment of osteoarthritis |
US9487511B2 (en) | 2014-04-11 | 2016-11-08 | Takeda Pharmaceutical Company Limited | Cyclopropanamine compound and use thereof |
US20210345613A1 (en) * | 2016-07-28 | 2021-11-11 | Basf Se | Herbicidal pyrimidine compounds |
CN109535019B (zh) * | 2017-09-21 | 2021-08-20 | 华东师范大学 | 1,1a,6,6a-四氢环丙并[a]茚-1-胺衍生物及其制备方法与应用 |
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GB1047268A (ru) | 1963-05-16 | |||
KR980009238A (ko) | 1995-07-28 | 1998-04-30 | 우에노 도시오 | 설포닐아미노산 유도체 |
ES2284180T3 (es) | 1996-01-23 | 2007-11-01 | SHIONOGI & CO., LTD. | Derivados de aminoacidos sulfonados e inhibidores de metaloproteinasas que contienen los mismos. |
US6696449B2 (en) * | 1997-03-04 | 2004-02-24 | Pharmacia Corporation | Sulfonyl aryl hydroxamates and their use as matrix metalloprotease inhibitors |
ES2176913T3 (es) | 1997-08-08 | 2002-12-01 | Pfizer Prod Inc | Derivados de acidos arilsulfonilaminohidroxamicos. |
HRP980443A2 (en) * | 1997-08-18 | 1999-10-31 | Carl P. Decicco | Novel inhibitors of aggrecanase and matrix metalloproteinases for the treatment of arthritis |
JP2000319250A (ja) * | 1998-04-03 | 2000-11-21 | Sankyo Co Ltd | スルホンアミド誘導体 |
US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
EP1081137A1 (en) * | 1999-08-12 | 2001-03-07 | Pfizer Products Inc. | Selective inhibitors of aggrecanase in osteoarthritis treatment |
DK1088819T3 (da) * | 1999-09-30 | 2005-09-12 | Pfizer Prod Inc | 6-azauracilderivater som thyroidreceptorligander |
AU2284001A (en) | 1999-12-27 | 2001-07-09 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted aminoalkylamide derivatives as antagonists of follicle stimulating hormone |
CN1366524A (zh) | 2000-04-07 | 2002-08-28 | 三星电子株式会社 | 磺胺衍生物作为基质金属蛋白酶抑制剂 |
JP2002284686A (ja) * | 2001-03-28 | 2002-10-03 | Sankyo Co Ltd | スルホンアミド化合物を含有する医薬組成物 |
AR040928A1 (es) * | 2001-05-11 | 2005-04-27 | Pharmacia Corp | Compuestos de acidos sulfona-hidroxamicos aromaticos, composiciones farmaceuticas y su uso en la preparacion de medicamentos utiles como inhibidores de proteasas |
EP1480946A2 (en) * | 2001-07-09 | 2004-12-01 | MP Biomedicals, L.L.C. | A hydroxamic acid thrombospondin peptide analog that inhibits aggrecanase activity |
US6683078B2 (en) * | 2001-07-19 | 2004-01-27 | Pharmacia Corporation | Use of sulfonyl aryl or heteroaryl hydroxamic acids and derivatives thereof as aggrecanase inhibitors |
PE20030701A1 (es) * | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
JP2006511500A (ja) * | 2002-10-30 | 2006-04-06 | メルク エンド カムパニー インコーポレーテッド | γ−アミノアミド系のケモカイン受容体活性調節剤 |
AU2003296993A1 (en) * | 2002-12-13 | 2004-07-09 | Smithkline Beecham Corporation | Cyclopropyl compounds as ccr5 antagonists |
US7317032B2 (en) * | 2003-09-02 | 2008-01-08 | Bristol-Myers Squibb Co. | Imidazolyl inhibitors of 15-lipoxygenase |
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US20060199826A1 (en) | 2006-09-07 |
JP2007516982A (ja) | 2007-06-28 |
EP1694410A2 (en) | 2006-08-30 |
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US20080261994A1 (en) | 2008-10-23 |
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AU2004299455A1 (en) | 2005-06-30 |
RU2006125441A (ru) | 2008-01-27 |
WO2005058884A2 (en) | 2005-06-30 |
US20100105894A1 (en) | 2010-04-29 |
ATE464286T1 (de) | 2010-04-15 |
CN1901971A (zh) | 2007-01-24 |
WO2005058884A3 (en) | 2005-09-09 |
EP1694410B1 (en) | 2010-04-14 |
DE602004026629D1 (de) | 2010-05-27 |
IL176247A0 (en) | 2006-10-05 |
US7351825B2 (en) | 2008-04-01 |
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