JP5567268B2 - Ｃｒｔｈ２の調節剤としての三環系スピロ誘導体 - Google Patents

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Publication number

JP5567268B2

JP5567268B2 JP2008512832A JP2008512832A JP5567268B2 JP 5567268 B2 JP5567268 B2 JP 5567268B2 JP 2008512832 A JP2008512832 A JP 2008512832A JP 2008512832 A JP2008512832 A JP 2008512832A JP 5567268 B2 JP5567268 B2 JP 5567268B2

Authority

JP

Japan

Prior art keywords

chloro

indole

acetic acid

trioxospiro

pyrrolidin

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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• 102000009389 Prostaglandin D receptors Human genes 0.000 title claims description 41
• 108050000258 Prostaglandin D receptors Proteins 0.000 title claims description 41
• 125000003003 spiro group Chemical group 0.000 title claims description 37
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 304
• 150000001875 compounds Chemical class 0.000 claims description 261
• 238000000034 method Methods 0.000 claims description 168
• -1 methoxy-substituted phenyl Chemical class 0.000 claims description 147
• 125000001072 heteroaryl group Chemical group 0.000 claims description 58
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
• 239000002585 base Substances 0.000 claims description 35
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 33
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 19
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 19
• 230000002757 inflammatory effect Effects 0.000 claims description 18
• 206010012442 Dermatitis contact Diseases 0.000 claims description 17
• 208000026935 allergic disease Diseases 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 230000000694 effects Effects 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 201000004624 Dermatitis Diseases 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 208000024376 chronic urticaria Diseases 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 208000002029 allergic contact dermatitis Diseases 0.000 claims description 12
• 208000010247 contact dermatitis Diseases 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 208000006673 asthma Diseases 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 208000017983 photosensitivity disease Diseases 0.000 claims description 11
• 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 10
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 201000008937 atopic dermatitis Diseases 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 206010061218 Inflammation Diseases 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 8
• 125000004093 cyano group Chemical class *C#N 0.000 claims description 8
• 230000004054 inflammatory process Effects 0.000 claims description 8
• 230000004770 neurodegeneration Effects 0.000 claims description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
• 125000004442 acylamino group Chemical class 0.000 claims description 7
• 201000009961 allergic asthma Diseases 0.000 claims description 7
• 208000004296 neuralgia Diseases 0.000 claims description 7
• 208000021722 neuropathic pain 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
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
• 206010052568 Urticaria chronic Diseases 0.000 claims description 6
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 6
• 201000010105 allergic rhinitis Diseases 0.000 claims description 6
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 6
• 208000029407 autoimmune urticaria Diseases 0.000 claims description 6
• 201000005884 exanthem Diseases 0.000 claims description 6
• 201000006417 multiple sclerosis Diseases 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 206010037844 rash Diseases 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 230000001568 sexual effect Effects 0.000 claims description 5
• 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 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 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 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
• 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 description 3
• 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 description 3
• 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 description 3
• DCLSTTYWFRSIQH-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-[[3-(trifluoromethyl)phenyl]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)N1CC1=CC=CC(C(F)(F)F)=C1 DCLSTTYWFRSIQH-UHFFFAOYSA-N 0.000 claims description 3
• ZXVGBYFMGIFZSF-UHFFFAOYSA-N 2-[5-chloro-2,2',5'-trioxo-1'-[[4-(trifluoromethyl)phenyl]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)N1CC1=CC=C(C(F)(F)F)C=C1 ZXVGBYFMGIFZSF-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• RQSLCLGHMUZKAM-UHFFFAOYSA-N 4-[5-chloro-1'-[(4-chlorophenyl)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=C(Cl)C=C1 RQSLCLGHMUZKAM-UHFFFAOYSA-N 0.000 claims description 3
• NOLYCSGPQXLBPU-UHFFFAOYSA-N 4-[5-chloro-1'-[(4-methoxyphenyl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]butanoic acid Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CCCC(O)=O)C2=O)CC1=O NOLYCSGPQXLBPU-UHFFFAOYSA-N 0.000 claims description 3
• SXVHRAIIPDCCEK-UHFFFAOYSA-N CCCCN1C2=C(C=C(C=C2)Cl)C3(C1=O)CC(=O)N(C3=O)CC4=CC=C(C=C4)C(F)(F)F Chemical compound CCCCN1C2=C(C=C(C=C2)Cl)C3(C1=O)CC(=O)N(C3=O)CC4=CC=C(C=C4)C(F)(F)F SXVHRAIIPDCCEK-UHFFFAOYSA-N 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• XYJDQXLCZDEIKO-UHFFFAOYSA-N 2-[5-chloro-1'-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound CC1=NOC(C)=C1CN1C(=O)C2(C3=CC(Cl)=CC=C3N(CC(O)=O)C2=O)CC1=O XYJDQXLCZDEIKO-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• ANRHUSRXUNPSER-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-chloropyridin-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=CC=C1Cl ANRHUSRXUNPSER-UHFFFAOYSA-N 0.000 claims description 2
• AZUYWGBLJPEIRR-UHFFFAOYSA-N 2-[5-chloro-1'-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,2',5'-trioxospiro[indole-3,3'-pyrrolidine]-1-yl]acetic acid Chemical compound COC1=C(C)C=NC(CN2C(C3(CC2=O)C2=CC(Cl)=CC=C2N(CC(O)=O)C3=O)=O)=C1C AZUYWGBLJPEIRR-UHFFFAOYSA-N 0.000 claims description 2
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