CA2602965C - Tricyclic spiro derivatives as crth2 modulators - Google Patents

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Publication number

CA2602965C

CA2602965C CA2602965A CA2602965A CA2602965C CA 2602965 C CA2602965 C CA 2602965C CA 2602965 A CA2602965 A CA 2602965A CA 2602965 A CA2602965 A CA 2602965A CA 2602965 C CA2602965 C CA 2602965C

Authority

CA

Canada

Prior art keywords

chloro

indole

pyrrolidin

acetic acid

trioxospiro

Prior art date

2005-05-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 125000003003 spiro group Chemical group 0.000 title abstract description 93
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 20
• 208000026935 allergic disease Diseases 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 201000010099 disease Diseases 0.000 claims abstract description 14
• 230000000694 effects Effects 0.000 claims abstract description 14
• 208000017520 skin disease Diseases 0.000 claims abstract description 13
• 230000002265 prevention Effects 0.000 claims abstract description 6
• 102000009389 Prostaglandin D receptors Human genes 0.000 claims abstract description 4
• 108050000258 Prostaglandin D receptors Proteins 0.000 claims abstract description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 730
• 150000001875 compounds Chemical class 0.000 claims description 260
• 238000000034 method Methods 0.000 claims description 108
• -1 aryl C1-C6-alkyl Chemical group 0.000 claims description 93
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• 125000003118 aryl group Chemical group 0.000 claims description 73
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
• 208000024376 chronic urticaria Diseases 0.000 claims description 18
• 230000029936 alkylation Effects 0.000 claims description 15
• 238000005804 alkylation reaction Methods 0.000 claims description 15
• 230000008569 process Effects 0.000 claims description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
• 208000006673 asthma Diseases 0.000 claims description 11
• 208000017983 photosensitivity disease Diseases 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 150000002431 hydrogen Chemical group 0.000 claims description 10
• 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims description 9
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
• 201000008937 atopic dermatitis Diseases 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 206010012442 Dermatitis contact Diseases 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 206010052568 Urticaria chronic Diseases 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 201000009961 allergic asthma Diseases 0.000 claims description 7
• 208000002029 allergic contact dermatitis Diseases 0.000 claims description 7
• 208000010247 contact dermatitis Diseases 0.000 claims description 7
• 206010037844 rash Diseases 0.000 claims description 7
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 6
• 208000010201 Exanthema Diseases 0.000 claims description 6
• 201000002481 Myositis Diseases 0.000 claims description 6
• QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical compound N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 claims description 6
• 206010051246 Photodermatosis Diseases 0.000 claims description 6
• 206010036087 Polymorphic light eruption Diseases 0.000 claims description 6
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 6
• 201000010105 allergic rhinitis Diseases 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 6
• 208000029407 autoimmune urticaria Diseases 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 6
• 201000005884 exanthem Diseases 0.000 claims description 6
• 201000006417 multiple sclerosis Diseases 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• 230000007062 hydrolysis Effects 0.000 claims description 5
• 238000006460 hydrolysis reaction Methods 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 3
• KCCHKYLQIKGUPB-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(1-phenylethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound O=C1CC2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)C(=O)N1C(C)C1=CC=CC=C1 KCCHKYLQIKGUPB-UHFFFAOYSA-N 0.000 claims description 3
• 230000001684 chronic effect Effects 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• 150000003456 sulfonamides Chemical class 0.000 claims description 3
• SXRCDONAJOPGQC-UHFFFAOYSA-N 2-[1'-(1,3-benzothiazol-2-ylmethyl)-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2SC3=CC=CC=C3N=2)C(=O)C1 SXRCDONAJOPGQC-UHFFFAOYSA-N 0.000 claims description 2
• VPIOMNUUAVOVBL-UHFFFAOYSA-N 2-[1'-(naphthalen-1-ylmethyl)-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2C3=CC=CC=C3C=CC=2)C(=O)C1 VPIOMNUUAVOVBL-UHFFFAOYSA-N 0.000 claims description 2
• AHJHZJYPIYKOIX-UHFFFAOYSA-N 2-[5'-chloro-1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-2,2',5-trioxospiro[imidazolidine-4,3'-indole]-1'-yl]acetic acid Chemical compound O=C1NC2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)C(=O)N1CC1=C(C)ON=C1C1=CC=CC=C1 AHJHZJYPIYKOIX-UHFFFAOYSA-N 0.000 claims description 2
• BCOAEEPCEQQXHB-UHFFFAOYSA-N 2-[5-chloro-1'-(naphthalen-1-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2C3=CC=CC=C3C=CC=2)C(=O)C1 BCOAEEPCEQQXHB-UHFFFAOYSA-N 0.000 claims description 2
• HUADETLFVZSYQX-UHFFFAOYSA-N 2-[5-chloro-1'-[(1-methylbenzotriazol-5-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound O=C1N(CC(O)=O)C2=CC=C(Cl)C=C2C1(C1=O)CC(=O)N1CC1=CC=C2N(C)N=NC2=C1 HUADETLFVZSYQX-UHFFFAOYSA-N 0.000 claims description 2
• KANZJDBAFHPYNR-QPJJXVBHSA-N 2-[5-chloro-2,2',5'-trioxo-1'-[(e)-3-phenylprop-2-enyl]spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1C\C=C\C1=CC=CC=C1 KANZJDBAFHPYNR-QPJJXVBHSA-N 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
• SKLDVYDFQCXARY-UHFFFAOYSA-N 2-[5-chloro-1'-[(2-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC=C1F SKLDVYDFQCXARY-UHFFFAOYSA-N 0.000 claims 2
• HIJZDZLPNFKWAV-UHFFFAOYSA-N 4-[5-chloro-1'-[(2-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]butanoic acid Chemical compound C12=CC(Cl)=CC=C2N(CCCC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC=C1F HIJZDZLPNFKWAV-UHFFFAOYSA-N 0.000 claims 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
• BDWQUHFLKUXBHZ-UHFFFAOYSA-N 2-(1'-benzyl-5-chloro-2,2'-dioxospiro[indole-3,4'-pyrrolidine]-1-yl)acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(CC1=O)CN1CC1=CC=CC=C1 BDWQUHFLKUXBHZ-UHFFFAOYSA-N 0.000 claims 1
• ZKFOWGQOVKDGDK-UHFFFAOYSA-N 2-(1'-but-2-ynyl-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl)acetic acid Chemical compound O=C1N(CC#CC)C(=O)CC21C1=CC(Cl)=CC=C1N(CC(O)=O)C2=O ZKFOWGQOVKDGDK-UHFFFAOYSA-N 0.000 claims 1
• DTHXODZAZAIWJB-UHFFFAOYSA-N 2-(1-benzyl-5'-chloro-2,2',5-trioxospiro[imidazolidine-4,3'-indole]-1'-yl)acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)NC(=O)N1CC1=CC=CC=C1 DTHXODZAZAIWJB-UHFFFAOYSA-N 0.000 claims 1
• ZCDQMYGMUJCSPB-HXUWFJFHSA-N 2-[(3r)-1'-benzyl-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC=CC=C1 ZCDQMYGMUJCSPB-HXUWFJFHSA-N 0.000 claims 1
• SKLDVYDFQCXARY-HXUWFJFHSA-N 2-[(3r)-5-chloro-1'-[(2-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC=CC=C1F SKLDVYDFQCXARY-HXUWFJFHSA-N 0.000 claims 1
• PTGHDUZXAIHWGN-HXUWFJFHSA-N 2-[(3r)-5-chloro-1'-[(3-chlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC=CC(Cl)=C1 PTGHDUZXAIHWGN-HXUWFJFHSA-N 0.000 claims 1
• IJRKCYVJCJRDTH-OAQYLSRUSA-N 2-[(3r)-5-chloro-1'-[(3-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=CC=CC(CN2C([C@@]3(C4=CC(Cl)=CC=C4N(CC(O)=O)C3=O)CC2=O)=O)=C1 IJRKCYVJCJRDTH-OAQYLSRUSA-N 0.000 claims 1
• IXKFWNVFUXXEFY-HXUWFJFHSA-N 2-[(3r)-5-chloro-1'-[(5-chloro-2-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC(Cl)=CC=C1F IXKFWNVFUXXEFY-HXUWFJFHSA-N 0.000 claims 1
• ZCDQMYGMUJCSPB-FQEVSTJZSA-N 2-[(3s)-1'-benzyl-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC=CC=C1 ZCDQMYGMUJCSPB-FQEVSTJZSA-N 0.000 claims 1
• PTGHDUZXAIHWGN-FQEVSTJZSA-N 2-[(3s)-5-chloro-1'-[(3-chlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC=CC(Cl)=C1 PTGHDUZXAIHWGN-FQEVSTJZSA-N 0.000 claims 1
• IJRKCYVJCJRDTH-NRFANRHFSA-N 2-[(3s)-5-chloro-1'-[(3-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=CC=CC(CN2C([C@]3(C4=CC(Cl)=CC=C4N(CC(O)=O)C3=O)CC2=O)=O)=C1 IJRKCYVJCJRDTH-NRFANRHFSA-N 0.000 claims 1
• IXKFWNVFUXXEFY-FQEVSTJZSA-N 2-[(3s)-5-chloro-1'-[(5-chloro-2-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C([C@]1(C(=O)N(C2=CC=C(Cl)C=C21)CC(=O)O)C1=O)C(=O)N1CC1=CC(Cl)=CC=C1F IXKFWNVFUXXEFY-FQEVSTJZSA-N 0.000 claims 1
• MIZGYGQQDQJKQN-UHFFFAOYSA-N 2-[1'-[(2-fluorophenyl)methyl]-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC=C1F MIZGYGQQDQJKQN-UHFFFAOYSA-N 0.000 claims 1
• FNYXTMPTHWWJIN-UHFFFAOYSA-N 2-[1'-[(3-fluorophenyl)methyl]-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC(F)=C1 FNYXTMPTHWWJIN-UHFFFAOYSA-N 0.000 claims 1
• HLKOBRAMJFIEGK-UHFFFAOYSA-N 2-[1'-[(4-acetamidophenyl)methyl]-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(NC(=O)C)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O HLKOBRAMJFIEGK-UHFFFAOYSA-N 0.000 claims 1
• FRNKZMPGRLAFSU-UHFFFAOYSA-N 2-[1'-[(4-carbamoylphenyl)methyl]-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(C(=O)N)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O FRNKZMPGRLAFSU-UHFFFAOYSA-N 0.000 claims 1
• BJZGPBBZPOZEAY-UHFFFAOYSA-N 2-[1'-[(4-chlorophenyl)methyl]-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(Cl)C=C1 BJZGPBBZPOZEAY-UHFFFAOYSA-N 0.000 claims 1
• OMZNSFXGTFCYFB-UHFFFAOYSA-N 2-[1'-[(4-fluorophenyl)methyl]-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(F)C=C1 OMZNSFXGTFCYFB-UHFFFAOYSA-N 0.000 claims 1
• MERNDDFNKCVMGC-UHFFFAOYSA-N 2-[1'-[(4-methoxyphenyl)methyl]-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2(C3=CC(OC(F)(F)F)=CC=C3N(CC(O)=O)C2=O)CC1=O MERNDDFNKCVMGC-UHFFFAOYSA-N 0.000 claims 1
• SYZBWTOXLKZZNP-UHFFFAOYSA-N 2-[1'-[(5-tert-butyl-1,2,4-oxadiazol-3-yl)methyl]-5-chloro-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound O1C(C(C)(C)C)=NC(CN2C(C3(CC2=O)C2=CC(Cl)=CC=C2N(CC(O)=O)C3=O)=O)=N1 SYZBWTOXLKZZNP-UHFFFAOYSA-N 0.000 claims 1
• SIFGTWUNWFVQMI-UHFFFAOYSA-N 2-[1'-benzyl-2,2',5'-trioxo-5-(trifluoromethoxy)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC=C1 SIFGTWUNWFVQMI-UHFFFAOYSA-N 0.000 claims 1
• ROGMHOCRIGQYMM-UHFFFAOYSA-N 2-[2,2',5'-trioxo-5-(trifluoromethoxy)-1'-[[3-(trifluoromethyl)phenyl]methyl]spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(OC(F)(F)F)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC(C(F)(F)F)=C1 ROGMHOCRIGQYMM-UHFFFAOYSA-N 0.000 claims 1
• RBHSFPBPZVMKMC-UHFFFAOYSA-N 2-[5'-chloro-1-[(2-fluorophenyl)methyl]-2,2',5-trioxospiro[imidazolidine-4,3'-indole]-1'-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)NC(=O)N1CC1=CC=CC=C1F RBHSFPBPZVMKMC-UHFFFAOYSA-N 0.000 claims 1
• HORZMXGVSURXCK-UHFFFAOYSA-N 2-[5'-chloro-1-[(5-chloro-2-fluorophenyl)methyl]-2,2',5-trioxospiro[imidazolidine-4,3'-indole]-1'-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)NC(=O)N1CC1=CC(Cl)=CC=C1F HORZMXGVSURXCK-UHFFFAOYSA-N 0.000 claims 1
• VEEDEOIGYMFLIJ-UHFFFAOYSA-N 2-[5-chloro-1'-(1,3-oxazol-2-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=NC=CO1 VEEDEOIGYMFLIJ-UHFFFAOYSA-N 0.000 claims 1
• NXGGINSWMFMGAF-UHFFFAOYSA-N 2-[5-chloro-1'-(1h-indol-3-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2C3=CC=CC=C3NC=2)C(=O)C1 NXGGINSWMFMGAF-UHFFFAOYSA-N 0.000 claims 1
• BKVGSKUAVVSZKF-UHFFFAOYSA-N 2-[5-chloro-1'-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC2OC3=CC=CC=C3OC2)C(=O)C1 BKVGSKUAVVSZKF-UHFFFAOYSA-N 0.000 claims 1
• KMDYEGRZWDBDTE-UHFFFAOYSA-N 2-[5-chloro-1'-(2-ethoxyethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound O=C1N(CCOCC)C(=O)CC21C1=CC(Cl)=CC=C1N(CC(O)=O)C2=O KMDYEGRZWDBDTE-UHFFFAOYSA-N 0.000 claims 1
• RAJFUMSJKMAFSR-UHFFFAOYSA-N 2-[5-chloro-1'-(furan-3-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC=1C=COC=1 RAJFUMSJKMAFSR-UHFFFAOYSA-N 0.000 claims 1
• JVKOATTXUZLONV-UHFFFAOYSA-N 2-[5-chloro-1'-(imidazo[1,2-a]pyridin-2-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2N=C3C=CC=CN3C=2)C(=O)C1 JVKOATTXUZLONV-UHFFFAOYSA-N 0.000 claims 1
• XLHVLCAWJHDPNA-UHFFFAOYSA-N 2-[5-chloro-1'-(isoquinolin-1-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2C3=CC=CC=C3C=CN=2)C(=O)C1 XLHVLCAWJHDPNA-UHFFFAOYSA-N 0.000 claims 1
• KHFZOPYXWWBGDT-UHFFFAOYSA-N 2-[5-chloro-1'-(naphthalen-2-ylmethyl)-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2C=C3C=CC=CC3=CC=2)C(=O)C1 KHFZOPYXWWBGDT-UHFFFAOYSA-N 0.000 claims 1
• RJOQDNCZKQYIFC-UHFFFAOYSA-N 2-[5-chloro-1'-[(1-methylbenzimidazol-2-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC=C2N(C)C(CN3C(C4(CC3=O)C3=CC(Cl)=CC=C3N(CC(O)=O)C4=O)=O)=NC2=C1 RJOQDNCZKQYIFC-UHFFFAOYSA-N 0.000 claims 1
• BYOIJQJNYAFOCM-UHFFFAOYSA-N 2-[5-chloro-1'-[(1-methylimidazol-2-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound CN1C=CN=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O BYOIJQJNYAFOCM-UHFFFAOYSA-N 0.000 claims 1
• NVRJDPGUPURMJE-UHFFFAOYSA-N 2-[5-chloro-1'-[(2,3-difluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC(F)=C1F NVRJDPGUPURMJE-UHFFFAOYSA-N 0.000 claims 1
• HIUAOLPQRYMOSK-UHFFFAOYSA-N 2-[5-chloro-1'-[(2,4-dichlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(Cl)C=C1Cl HIUAOLPQRYMOSK-UHFFFAOYSA-N 0.000 claims 1
• ZFWNQCXXLVSIBW-UHFFFAOYSA-N 2-[5-chloro-1'-[(2,4-difluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(F)C=C1F ZFWNQCXXLVSIBW-UHFFFAOYSA-N 0.000 claims 1
• VITIJZLHMBHKEV-UHFFFAOYSA-N 2-[5-chloro-1'-[(2,5-dichlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(Cl)=CC=C1Cl VITIJZLHMBHKEV-UHFFFAOYSA-N 0.000 claims 1
• SWCNYWLKCRDUOM-UHFFFAOYSA-N 2-[5-chloro-1'-[(2,5-difluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(F)=CC=C1F SWCNYWLKCRDUOM-UHFFFAOYSA-N 0.000 claims 1
• OSWKOYHLOHUIKD-UHFFFAOYSA-N 2-[5-chloro-1'-[(2-chloro-4-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(F)C=C1Cl OSWKOYHLOHUIKD-UHFFFAOYSA-N 0.000 claims 1
• WNEFBNBADIHNTR-UHFFFAOYSA-N 2-[5-chloro-1'-[(2-chloro-5-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(F)=CC=C1Cl WNEFBNBADIHNTR-UHFFFAOYSA-N 0.000 claims 1
• AYLVIBHVUIINDQ-UHFFFAOYSA-N 2-[5-chloro-1'-[(2-fluorophenyl)methyl]-2,2'-dioxospiro[indole-3,4'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(CC1=O)CN1CC1=CC=CC=C1F AYLVIBHVUIINDQ-UHFFFAOYSA-N 0.000 claims 1
• MGAOEUROKBHMFA-UHFFFAOYSA-N 2-[5-chloro-1'-[(2-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=CC=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O MGAOEUROKBHMFA-UHFFFAOYSA-N 0.000 claims 1
• VFEFRCZEARGBHS-UHFFFAOYSA-N 2-[5-chloro-1'-[(2-methyl-1,3-thiazol-4-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound S1C(C)=NC(CN2C(C3(CC2=O)C2=CC(Cl)=CC=C2N(CC(O)=O)C3=O)=O)=C1 VFEFRCZEARGBHS-UHFFFAOYSA-N 0.000 claims 1
• JMZRHDAWVDSWQF-UHFFFAOYSA-N 2-[5-chloro-1'-[(3,4-dichlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(Cl)C(Cl)=C1 JMZRHDAWVDSWQF-UHFFFAOYSA-N 0.000 claims 1
• PTFFTFCAJUGNCA-UHFFFAOYSA-N 2-[5-chloro-1'-[(3,4-difluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(F)C(F)=C1 PTFFTFCAJUGNCA-UHFFFAOYSA-N 0.000 claims 1
• OWXURLWMLGLCRG-UHFFFAOYSA-N 2-[5-chloro-1'-[(3,4-dimethoxypyridin-2-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=CC=NC(CN2C(C3(C4=CC(Cl)=CC=C4N(CC(O)=O)C3=O)CC2=O)=O)=C1OC OWXURLWMLGLCRG-UHFFFAOYSA-N 0.000 claims 1
• VOCJBWXZCOYCSS-UHFFFAOYSA-N 2-[5-chloro-1'-[(3,5-dichlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(Cl)=CC(Cl)=C1 VOCJBWXZCOYCSS-UHFFFAOYSA-N 0.000 claims 1
• NPZVEIRNQWICMX-UHFFFAOYSA-N 2-[5-chloro-1'-[(3,5-difluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(F)=CC(F)=C1 NPZVEIRNQWICMX-UHFFFAOYSA-N 0.000 claims 1
• LPIWZNGOWJMOET-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-chloro-5-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(F)=CC(Cl)=C1 LPIWZNGOWJMOET-UHFFFAOYSA-N 0.000 claims 1
• PTGHDUZXAIHWGN-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-chlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC(Cl)=C1 PTGHDUZXAIHWGN-UHFFFAOYSA-N 0.000 claims 1
• XYBOUFBPQGOIKA-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-cyanophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC(C#N)=C1 XYBOUFBPQGOIKA-UHFFFAOYSA-N 0.000 claims 1
• GKGDSCNLTJTSRM-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-fluoro-4-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=C(F)C(OC)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O GKGDSCNLTJTSRM-UHFFFAOYSA-N 0.000 claims 1
• NLKAUARGFHANJP-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC(F)=C1 NLKAUARGFHANJP-UHFFFAOYSA-N 0.000 claims 1
• IJRKCYVJCJRDTH-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=CC=CC(CN2C(C3(C4=CC(Cl)=CC=C4N(CC(O)=O)C3=O)CC2=O)=O)=C1 IJRKCYVJCJRDTH-UHFFFAOYSA-N 0.000 claims 1
• LXGNNQDDJMZRPP-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-methyl-5-phenyl-1,2-oxazol-4-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound O=C1CC2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)C(=O)N1CC=1C(C)=NOC=1C1=CC=CC=C1 LXGNNQDDJMZRPP-UHFFFAOYSA-N 0.000 claims 1
• UJYVUWBBXAPUDC-UHFFFAOYSA-N 2-[5-chloro-1'-[(3-methyl-5-phenyl-1,2-oxazol-4-yl)methyl]-2,2'-dioxospiro[indole-3,4'-pyrrolidine]-1-yl]acetic acid Chemical compound C1C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC(=O)N1CC=1C(C)=NOC=1C1=CC=CC=C1 UJYVUWBBXAPUDC-UHFFFAOYSA-N 0.000 claims 1
• YVCKPHCPPACAIN-UHFFFAOYSA-N 2-[5-chloro-1'-[(4,6-dichloropyridin-3-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CN=C(Cl)C=C1Cl YVCKPHCPPACAIN-UHFFFAOYSA-N 0.000 claims 1
• SBBKJNZAFBHKLP-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-chlorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(Cl)C=C1 SBBKJNZAFBHKLP-UHFFFAOYSA-N 0.000 claims 1
• SUQRWQPFUBHAPC-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-cyanophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(C#N)C=C1 SUQRWQPFUBHAPC-UHFFFAOYSA-N 0.000 claims 1
• YTCBTHYXIOAOBE-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=C(F)C=C1 YTCBTHYXIOAOBE-UHFFFAOYSA-N 0.000 claims 1
• WBTUGPRALHNURF-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-methoxy-3-methylpyridin-2-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=CC=NC(CN2C(C3(CC2=O)C2=CC(Cl)=CC=C2N(CC(O)=O)C3=O)=O)=C1C WBTUGPRALHNURF-UHFFFAOYSA-N 0.000 claims 1
• JMRWMHANGPLKDK-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O JMRWMHANGPLKDK-UHFFFAOYSA-N 0.000 claims 1
• FIYAWIMSRGXCQW-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-methylphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(C)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O FIYAWIMSRGXCQW-UHFFFAOYSA-N 0.000 claims 1
• ZBGGRYYJOCXSEE-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-methylsulfonylphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O ZBGGRYYJOCXSEE-UHFFFAOYSA-N 0.000 claims 1
• IXKFWNVFUXXEFY-UHFFFAOYSA-N 2-[5-chloro-1'-[(5-chloro-2-fluorophenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC(Cl)=CC=C1F IXKFWNVFUXXEFY-UHFFFAOYSA-N 0.000 claims 1
• ABVCZPJCOYQLBK-UHFFFAOYSA-N 2-[5-chloro-1'-[(5-chloro-2-fluorophenyl)methyl]-2,2'-dioxospiro[indole-3,4'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(CC1=O)CN1CC1=CC(Cl)=CC=C1F ABVCZPJCOYQLBK-UHFFFAOYSA-N 0.000 claims 1
• GJBXQPUEBHEYHM-UHFFFAOYSA-N 2-[5-chloro-1'-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound O=C1CC2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)C(=O)N1CC1=C(C)ON=C1C1=CC=CC=C1 GJBXQPUEBHEYHM-UHFFFAOYSA-N 0.000 claims 1
• NWLZEVBSBHXJKF-UHFFFAOYSA-N 2-[5-chloro-1'-[[2-(3-chlorophenyl)-1,3-thiazol-4-yl]methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC(N=1)=CSC=1C1=CC=CC(Cl)=C1 NWLZEVBSBHXJKF-UHFFFAOYSA-N 0.000 claims 1
• VJYXHXGNMCGAMT-UHFFFAOYSA-N 2-[5-chloro-1'-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 VJYXHXGNMCGAMT-UHFFFAOYSA-N 0.000 claims 1
• FNJGDJONLJMSIZ-UHFFFAOYSA-N 2-[5-chloro-1'-[[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(CN2C(C3(CC2=O)C2=CC(Cl)=CC=C2N(CC(O)=O)C3=O)=O)=NO1 FNJGDJONLJMSIZ-UHFFFAOYSA-N 0.000 claims 1
• RFZWHXXLQZQHGG-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(1,3-thiazol-4-ylmethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CSC=N1 RFZWHXXLQZQHGG-UHFFFAOYSA-N 0.000 claims 1
• KYPFARHSDHLLCC-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(2-phenoxyethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CCOC1=CC=CC=C1 KYPFARHSDHLLCC-UHFFFAOYSA-N 0.000 claims 1
• GCKMETBVGIPQGI-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CCC1=CC=CC=C1 GCKMETBVGIPQGI-UHFFFAOYSA-N 0.000 claims 1
• PYRNQDMFWBYXHV-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(2-phenylmethoxyethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CCOCC1=CC=CC=C1 PYRNQDMFWBYXHV-UHFFFAOYSA-N 0.000 claims 1
• PWHVCCRSCHOVNJ-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(3-phenylprop-2-ynyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC#CC1=CC=CC=C1 PWHVCCRSCHOVNJ-UHFFFAOYSA-N 0.000 claims 1
• HAQDHFLSFYXEHU-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(pyridin-2-ylmethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CC=N1 HAQDHFLSFYXEHU-UHFFFAOYSA-N 0.000 claims 1
• MUISNBWDZPNXDE-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(pyridin-3-ylmethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CN=C1 MUISNBWDZPNXDE-UHFFFAOYSA-N 0.000 claims 1
• ZBLQINMHWPBDTQ-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(quinolin-2-ylmethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C11C(=O)N(CC=2N=C3C=CC=CC3=CC=2)C(=O)C1 ZBLQINMHWPBDTQ-UHFFFAOYSA-N 0.000 claims 1
• MAIOCNMQTWAEBE-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-(thiophen-2-ylmethyl)spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC1=CC=CS1 MAIOCNMQTWAEBE-UHFFFAOYSA-N 0.000 claims 1
• ABNOGVNXTHIDDC-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-[(2-phenyl-1,3-thiazol-4-yl)methyl]spiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(=O)O)C(=O)C1(C1=O)CC(=O)N1CC(N=1)=CSC=1C1=CC=CC=C1 ABNOGVNXTHIDDC-UHFFFAOYSA-N 0.000 claims 1
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