HRP20080022T4 - Derivati pirolopiridina i njihova upotreba kao crth2 antagonista - Google Patents
Derivati pirolopiridina i njihova upotreba kao crth2 antagonista Download PDFInfo
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- HRP20080022T4 HRP20080022T4 HR20080022T HRP20080022T HRP20080022T4 HR P20080022 T4 HRP20080022 T4 HR P20080022T4 HR 20080022 T HR20080022 T HR 20080022T HR P20080022 T HRP20080022 T HR P20080022T HR P20080022 T4 HRP20080022 T4 HR P20080022T4
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- HR
- Croatia
- Prior art keywords
- methyl
- pyridin
- pyrrolo
- acetic acid
- benzenesulfonyl
- Prior art date
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- 239000005557 antagonist Substances 0.000 title 1
- 150000005255 pyrrolopyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 150000003839 salts Chemical group 0.000 claims abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 239000012907 medicinal substance Substances 0.000 claims 3
- ADVSFOJYGBVTHV-UHFFFAOYSA-N 2-[1-[(2-methoxyphenyl)methyl]-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound COC1=CC=CC=C1CN1C2=NC=CC=C2C(CC(O)=O)=C1C ADVSFOJYGBVTHV-UHFFFAOYSA-N 0.000 claims 2
- KDVHQSDKFPRKOR-UHFFFAOYSA-N 2-[1-[(4-methoxyphenyl)methyl]-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=CC=C2C(CC(O)=O)=C1C KDVHQSDKFPRKOR-UHFFFAOYSA-N 0.000 claims 2
- HGOCBGDTYMERHN-UHFFFAOYSA-N 2-[2-methyl-1-[1-(4-methylsulfonylphenyl)ethyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1C(C)C1=CC=C(S(C)(=O)=O)C=C1 HGOCBGDTYMERHN-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000001387 anti-histamine Effects 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 229940124630 bronchodilator Drugs 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- -1 (2-methyl-1-pyridin-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- RMCCJXQIDFNMIV-UHFFFAOYSA-N 2-(1-benzyl-2-methylpyrrolo[2,3-b]pyridin-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=CC=C1 RMCCJXQIDFNMIV-UHFFFAOYSA-N 0.000 claims 1
- JHLJSIJMBUMXCC-UHFFFAOYSA-N 2-(2-methyl-1-naphthalen-2-ylsulfonylpyrrolo[2,3-b]pyridin-3-yl)acetic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)N3C4=NC=CC=C4C(CC(O)=O)=C3C)=CC=C21 JHLJSIJMBUMXCC-UHFFFAOYSA-N 0.000 claims 1
- GGGQAPQTJWRTPY-UHFFFAOYSA-N 2-(2-methyl-1-pyridin-3-ylsulfonylpyrrolo[2,3-b]pyridin-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CN=C1 GGGQAPQTJWRTPY-UHFFFAOYSA-N 0.000 claims 1
- TVIDARLZEKWIMB-UHFFFAOYSA-N 2-(2-methyl-1-thiophen-2-ylsulfonylpyrrolo[2,3-b]pyridin-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CS1 TVIDARLZEKWIMB-UHFFFAOYSA-N 0.000 claims 1
- ZWVMEUHVVKNEKQ-UHFFFAOYSA-N 2-[1-(1-benzofuran-2-ylmethyl)-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=CC=C2OC(CN3C4=NC=CC=C4C(CC(O)=O)=C3C)=CC2=C1 ZWVMEUHVVKNEKQ-UHFFFAOYSA-N 0.000 claims 1
- NRBUALHZASRZRS-UHFFFAOYSA-N 2-[1-(2,3-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1Cl NRBUALHZASRZRS-UHFFFAOYSA-N 0.000 claims 1
- HPMSCHQGILNBLR-UHFFFAOYSA-N 2-[1-(2,4-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C=C1Cl HPMSCHQGILNBLR-UHFFFAOYSA-N 0.000 claims 1
- XOXARJQYPKGSMK-UHFFFAOYSA-N 2-[1-(2,4-difluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(F)C=C1F XOXARJQYPKGSMK-UHFFFAOYSA-N 0.000 claims 1
- FEMJAPKOEULTMA-UHFFFAOYSA-N 2-[1-(2,5-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC(Cl)=CC=C1Cl FEMJAPKOEULTMA-UHFFFAOYSA-N 0.000 claims 1
- QRFRXPYTXHJZRI-UHFFFAOYSA-N 2-[1-(2,5-dichlorothiophen-3-yl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C=1C=C(Cl)SC=1Cl QRFRXPYTXHJZRI-UHFFFAOYSA-N 0.000 claims 1
- SCDJEDNDYPJVKZ-UHFFFAOYSA-N 2-[1-(2-chloro-4-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C#N)C=C1Cl SCDJEDNDYPJVKZ-UHFFFAOYSA-N 0.000 claims 1
- JAACRELBVGKWOB-UHFFFAOYSA-N 2-[1-(2-chloro-4-fluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(F)C=C1Cl JAACRELBVGKWOB-UHFFFAOYSA-N 0.000 claims 1
- AZVZHSDDZRNXFE-UHFFFAOYSA-N 2-[1-(2-chloro-5-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC(C#N)=CC=C1Cl AZVZHSDDZRNXFE-UHFFFAOYSA-N 0.000 claims 1
- LLJRFZGQADBFGY-UHFFFAOYSA-N 2-[1-(2-chloro-5-methoxyphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1 LLJRFZGQADBFGY-UHFFFAOYSA-N 0.000 claims 1
- AVIOUBLZXHFINY-UHFFFAOYSA-N 2-[1-(2-chlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC=C1Cl AVIOUBLZXHFINY-UHFFFAOYSA-N 0.000 claims 1
- CQXMJRURHXVTEZ-UHFFFAOYSA-N 2-[1-(2-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC=C1C#N CQXMJRURHXVTEZ-UHFFFAOYSA-N 0.000 claims 1
- GHGWUGPMLIZEBR-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC=C1F GHGWUGPMLIZEBR-UHFFFAOYSA-N 0.000 claims 1
- PGQJAOVZTMGUMW-UHFFFAOYSA-N 2-[1-(2-methoxycarbonylthiophen-3-yl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound S1C=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1C(=O)OC PGQJAOVZTMGUMW-UHFFFAOYSA-N 0.000 claims 1
- GSZRZMZTHWSNFG-UHFFFAOYSA-N 2-[1-(3,4-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 GSZRZMZTHWSNFG-UHFFFAOYSA-N 0.000 claims 1
- BOPNUPOBQCNAOZ-UHFFFAOYSA-N 2-[1-(3,4-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]propanoic acid Chemical compound C12=NC=CC=C2C(C(C(O)=O)C)=C(C)N1S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 BOPNUPOBQCNAOZ-UHFFFAOYSA-N 0.000 claims 1
- UCKXEDVQMJRGCM-UHFFFAOYSA-N 2-[1-(3,4-dicyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C#N)C(C#N)=C1 UCKXEDVQMJRGCM-UHFFFAOYSA-N 0.000 claims 1
- HLSYGDSWXJGENX-UHFFFAOYSA-N 2-[1-(3,4-difluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(F)C(F)=C1 HLSYGDSWXJGENX-UHFFFAOYSA-N 0.000 claims 1
- LPZJWDHGAVFOAP-UHFFFAOYSA-N 2-[1-(3,5-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 LPZJWDHGAVFOAP-UHFFFAOYSA-N 0.000 claims 1
- SRFUHQQLOVEEKR-UHFFFAOYSA-N 2-[1-(3,5-difluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC(F)=CC(F)=C1 SRFUHQQLOVEEKR-UHFFFAOYSA-N 0.000 claims 1
- NSEZCWDESVRZGJ-UHFFFAOYSA-N 2-[1-(3-bromophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(Br)=C1 NSEZCWDESVRZGJ-UHFFFAOYSA-N 0.000 claims 1
- HTMOXGDZJFCWIS-UHFFFAOYSA-N 2-[1-(3-butoxy-4-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=C(C#N)C(OCCCC)=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1 HTMOXGDZJFCWIS-UHFFFAOYSA-N 0.000 claims 1
- LKCQHUUHAUWWKE-UHFFFAOYSA-N 2-[1-(3-chloro-2-methylphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1C LKCQHUUHAUWWKE-UHFFFAOYSA-N 0.000 claims 1
- XKUHOUKQLZISOW-UHFFFAOYSA-N 2-[1-(3-chloro-4-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C#N)C(Cl)=C1 XKUHOUKQLZISOW-UHFFFAOYSA-N 0.000 claims 1
- RXMROYPWKDYKEM-UHFFFAOYSA-N 2-[1-(3-chloro-4-fluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 RXMROYPWKDYKEM-UHFFFAOYSA-N 0.000 claims 1
- MYZJGZJKOHKHQV-UHFFFAOYSA-N 2-[1-(3-chloro-4-methylphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 MYZJGZJKOHKHQV-UHFFFAOYSA-N 0.000 claims 1
- NXVYLUHXXCIUGG-UHFFFAOYSA-N 2-[1-(3-chlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1 NXVYLUHXXCIUGG-UHFFFAOYSA-N 0.000 claims 1
- XRMUPVMLIVXXAW-UHFFFAOYSA-N 2-[1-(3-cyano-4-fluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(F)C(C#N)=C1 XRMUPVMLIVXXAW-UHFFFAOYSA-N 0.000 claims 1
- UVQSIENQOKEEBM-UHFFFAOYSA-N 2-[1-(3-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(C#N)=C1 UVQSIENQOKEEBM-UHFFFAOYSA-N 0.000 claims 1
- BJFJWYXVJMOCGC-UHFFFAOYSA-N 2-[1-(3-fluoro-2-methylphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(F)=C1C BJFJWYXVJMOCGC-UHFFFAOYSA-N 0.000 claims 1
- UODPWJGIGBXJAM-UHFFFAOYSA-N 2-[1-(3-fluoro-4-methylphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C)C(F)=C1 UODPWJGIGBXJAM-UHFFFAOYSA-N 0.000 claims 1
- UDJHZVKEFLDLSZ-UHFFFAOYSA-N 2-[1-(3-fluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(F)=C1 UDJHZVKEFLDLSZ-UHFFFAOYSA-N 0.000 claims 1
- YYLDZWDYGISHIY-UHFFFAOYSA-N 2-[1-(3-methoxyphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound COC1=CC=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1 YYLDZWDYGISHIY-UHFFFAOYSA-N 0.000 claims 1
- QXKDRNAWIJXBMQ-UHFFFAOYSA-N 2-[1-(4-chloro-2-fluoro-5-methoxyphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1F QXKDRNAWIJXBMQ-UHFFFAOYSA-N 0.000 claims 1
- KNAXYNVOPGKEKD-UHFFFAOYSA-N 2-[1-(4-chloro-3-cyanophenyl)sulfonyl-2-ethylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CCC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C(C#N)=C1 KNAXYNVOPGKEKD-UHFFFAOYSA-N 0.000 claims 1
- OZCGPVBNRJKAGT-UHFFFAOYSA-N 2-[1-(4-chloro-3-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C(C#N)=C1 OZCGPVBNRJKAGT-UHFFFAOYSA-N 0.000 claims 1
- ALBFBGXILYBHCK-UHFFFAOYSA-N 2-[1-(4-chloro-3-fluorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C(F)=C1 ALBFBGXILYBHCK-UHFFFAOYSA-N 0.000 claims 1
- AAOILMKPAAXMET-UHFFFAOYSA-N 2-[1-(4-chloro-3-methoxyphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1 AAOILMKPAAXMET-UHFFFAOYSA-N 0.000 claims 1
- CVTPGVYUROSFNI-UHFFFAOYSA-N 2-[1-(4-chloro-3-methylphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C(C)=C1 CVTPGVYUROSFNI-UHFFFAOYSA-N 0.000 claims 1
- UWPSBMVNCDNJND-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1C1=CC=C(Cl)C=C1 UWPSBMVNCDNJND-UHFFFAOYSA-N 0.000 claims 1
- SFUKQIBDQAEIQC-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C=C1 SFUKQIBDQAEIQC-UHFFFAOYSA-N 0.000 claims 1
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- DIQRXZWSBCYLQK-UHFFFAOYSA-N 2-[1-(4-cyano-3-methoxyphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC)=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1 DIQRXZWSBCYLQK-UHFFFAOYSA-N 0.000 claims 1
- ZBBWNEQTRIQYDU-UHFFFAOYSA-N 2-[1-(4-cyano-3-methylphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C#N)C(C)=C1 ZBBWNEQTRIQYDU-UHFFFAOYSA-N 0.000 claims 1
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- WGWLXUWTYYNCQR-UHFFFAOYSA-N 2-[1-(4-cyanophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C#N)C=C1 WGWLXUWTYYNCQR-UHFFFAOYSA-N 0.000 claims 1
- KLZALHRLXXRMDK-UHFFFAOYSA-N 2-[1-(4-fluoro-3-methoxyphenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=C(F)C(OC)=CC(S(=O)(=O)N2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1 KLZALHRLXXRMDK-UHFFFAOYSA-N 0.000 claims 1
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- FSNSTDVQWKJMHC-UHFFFAOYSA-N 2-[2-methyl-1-[(4-nitrophenyl)methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C([N+]([O-])=O)C=C1 FSNSTDVQWKJMHC-UHFFFAOYSA-N 0.000 claims 1
- XMCRMQJEYLGRKF-UHFFFAOYSA-N 2-[2-methyl-1-[(4-propan-2-ylsulfonylphenyl)methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C(C)C)=CC=C1CN1C2=NC=CC=C2C(CC(O)=O)=C1C XMCRMQJEYLGRKF-UHFFFAOYSA-N 0.000 claims 1
- JSIBHOMOVYVXLN-UHFFFAOYSA-N 2-[2-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound O1C(C)=CC(CN2C3=NC=CC=C3C(CC(O)=O)=C2C)=N1 JSIBHOMOVYVXLN-UHFFFAOYSA-N 0.000 claims 1
- ZIIBKQIEASHQES-UHFFFAOYSA-N 2-[2-methyl-1-[1-[4-(trifluoromethyl)phenyl]ethyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1C(C)C1=CC=C(C(F)(F)F)C=C1 ZIIBKQIEASHQES-UHFFFAOYSA-N 0.000 claims 1
- PKBLHDIUVGSSKR-UHFFFAOYSA-N 2-[2-methyl-1-[3-(trifluoromethoxy)phenyl]sulfonylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(OC(F)(F)F)=C1 PKBLHDIUVGSSKR-UHFFFAOYSA-N 0.000 claims 1
- NMFURNJWIQMNRK-UHFFFAOYSA-N 2-[2-methyl-1-[3-(trifluoromethyl)phenyl]sulfonylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 NMFURNJWIQMNRK-UHFFFAOYSA-N 0.000 claims 1
- JZAZWEBRRURSPV-UHFFFAOYSA-N 2-[2-methyl-1-[4-(trifluoromethyl)phenyl]sulfonylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 JZAZWEBRRURSPV-UHFFFAOYSA-N 0.000 claims 1
- MMVVMXRLSLWVAD-UHFFFAOYSA-N 2-[2-methyl-1-[[2-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=CC=C1C(F)(F)F MMVVMXRLSLWVAD-UHFFFAOYSA-N 0.000 claims 1
- UYIROIBHFFVNIV-UHFFFAOYSA-N 2-[2-methyl-1-[[3-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=CC(C(F)(F)F)=C1 UYIROIBHFFVNIV-UHFFFAOYSA-N 0.000 claims 1
- HHBHAJJFIBUNBJ-UHFFFAOYSA-N 2-[2-methyl-1-[[4-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C(C(F)(F)F)C=C1 HHBHAJJFIBUNBJ-UHFFFAOYSA-N 0.000 claims 1
- XTDBCVHBEDQJAK-UHFFFAOYSA-N 2-[2-methyl-1-[[4-(trifluoromethylsulfonyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 XTDBCVHBEDQJAK-UHFFFAOYSA-N 0.000 claims 1
- GFPPXZDRVCSVNR-UHFFFAOYSA-N 2-[2-methyl-1-[[4-methylsulfonyl-2-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C(S(C)(=O)=O)C=C1C(F)(F)F GFPPXZDRVCSVNR-UHFFFAOYSA-N 0.000 claims 1
- PRAHYBHEVROCIX-UHFFFAOYSA-N 2-[2-methyl-1-[[4-methylsulfonyl-3-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 PRAHYBHEVROCIX-UHFFFAOYSA-N 0.000 claims 1
- SDMJEKWSZNSQCU-UHFFFAOYSA-N 2-[2-methyl-1-[[5-methyl-2-(trifluoromethyl)furan-3-yl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound O1C(C)=CC(CN2C3=NC=CC=C3C(CC(O)=O)=C2C)=C1C(F)(F)F SDMJEKWSZNSQCU-UHFFFAOYSA-N 0.000 claims 1
- XABUZEJSQGVKOW-UHFFFAOYSA-N 2-[2-methyl-1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C(C(F)(F)F)N=C1 XABUZEJSQGVKOW-UHFFFAOYSA-N 0.000 claims 1
- OGYOFVOUGPSGAC-UHFFFAOYSA-N 2-[4-chloro-1-(3,4-dichlorophenyl)sulfonyl-2-methylpyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=C(Cl)C=CN=C2N1S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 OGYOFVOUGPSGAC-UHFFFAOYSA-N 0.000 claims 1
- BUBIAPCEJNADFR-UHFFFAOYSA-N 2-[4-chloro-2-methyl-1-[(4-methylsulfonylphenyl)methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=C(Cl)C=CN=C2N1CC1=CC=C(S(C)(=O)=O)C=C1 BUBIAPCEJNADFR-UHFFFAOYSA-N 0.000 claims 1
- GNWMYJHVDPIOAC-UHFFFAOYSA-N 2-[6-chloro-2-methyl-1-[(4-methylsulfonylphenyl)methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=C(Cl)N=C2N1CC1=CC=C(S(C)(=O)=O)C=C1 GNWMYJHVDPIOAC-UHFFFAOYSA-N 0.000 claims 1
- OBVVFBINKAZBAI-UHFFFAOYSA-N 2-[6-chloro-2-methyl-1-[[4-methylsulfonyl-2-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=C(Cl)N=C2N1CC1=CC=C(S(C)(=O)=O)C=C1C(F)(F)F OBVVFBINKAZBAI-UHFFFAOYSA-N 0.000 claims 1
- 206010027654 Allergic conditions Diseases 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- 230000000954 anitussive effect Effects 0.000 claims 1
- 229940124584 antitussives Drugs 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0413619A GB0413619D0 (en) | 2004-06-17 | 2004-06-17 | Organic compounds |
| GB0507693A GB0507693D0 (en) | 2005-04-15 | 2005-04-15 | Organic compounds |
| PCT/EP2005/006493 WO2005123731A2 (fr) | 2004-06-17 | 2005-06-16 | Composes organiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20080022T3 HRP20080022T3 (en) | 2008-02-29 |
| HRP20080022T4 true HRP20080022T4 (hr) | 2011-10-31 |
Family
ID=35510318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20080022T HRP20080022T4 (hr) | 2004-06-17 | 2008-01-16 | Derivati pirolopiridina i njihova upotreba kao crth2 antagonista |
Country Status (29)
| Country | Link |
|---|---|
| US (5) | US7666878B2 (fr) |
| EP (1) | EP1761529B3 (fr) |
| JP (1) | JP4886680B2 (fr) |
| KR (1) | KR101183330B1 (fr) |
| AR (1) | AR049443A1 (fr) |
| AT (1) | ATE378338T1 (fr) |
| AU (1) | AU2005254681B2 (fr) |
| BR (1) | BRPI0512060B8 (fr) |
| CA (1) | CA2569125C (fr) |
| CY (1) | CY1107851T1 (fr) |
| DE (1) | DE602005003365T3 (fr) |
| DK (1) | DK1761529T3 (fr) |
| EC (1) | ECSP067077A (fr) |
| ES (1) | ES2294717T7 (fr) |
| HK (1) | HK1103730A1 (fr) |
| HR (1) | HRP20080022T4 (fr) |
| IL (1) | IL179604A (fr) |
| MA (1) | MA28666B1 (fr) |
| MX (1) | MXPA06014694A (fr) |
| MY (1) | MY144903A (fr) |
| NO (1) | NO338319B1 (fr) |
| NZ (1) | NZ551439A (fr) |
| PE (1) | PE20060301A1 (fr) |
| PL (1) | PL1761529T6 (fr) |
| PT (1) | PT1761529E (fr) |
| RS (1) | RS50552B (fr) |
| RU (1) | RU2379309C2 (fr) |
| TW (1) | TWI352702B (fr) |
| WO (1) | WO2005123731A2 (fr) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY144903A (en) | 2004-06-17 | 2011-11-30 | Novartis Ag | Pyrrolopyridine derivatives and their use as crth2 antagonists |
| GB0525144D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525143D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525337D0 (en) * | 2005-12-13 | 2006-01-18 | Novartis Ag | Organic compounds |
| SI1986633T1 (sl) | 2006-02-10 | 2015-03-31 | Summit Corporation Plc | Zdravljenje Duchennove mišične distrofije |
| GB0611695D0 (en) * | 2006-06-13 | 2006-07-26 | Novartis Ag | Organic compounds |
| KR101411820B1 (ko) | 2006-08-07 | 2014-06-24 | 액테리온 파마슈티칼 리미티드 | (3-아미노-1,2,3,4-테트라하이드로-9ｈ-카르바졸-9-일)-아세트산 유도체 |
| JP2010535708A (ja) * | 2007-08-03 | 2010-11-25 | ビオマリン アイジーエー リミテッド | デュシェンヌ型筋ジストロフィーの治療のための薬物併用 |
| GB0715937D0 (en) * | 2007-08-15 | 2007-09-26 | Vastox Plc | Method of treatment og duchenne muscular dystrophy |
| WO2009102462A1 (fr) * | 2008-02-15 | 2009-08-20 | Abbott Laboratories | Thiénopyrroles et pyrrolothiazoles utilisés comme nouveaux agents thérapeutiques |
| JP5688366B2 (ja) | 2008-08-15 | 2015-03-25 | エヌサーティー・ファーマシューティカルズ・インコーポレーテッド | 治療薬剤としての、ｓ−ニトロソグルタチオンレダクターゼの新規ピロール阻害剤 |
| DK2315590T3 (da) | 2008-08-15 | 2012-11-19 | N30 Pharmaceuticals Inc | Pyrrolinhibitorer af S-nitrosoglutathionreduktase |
| HUE031580T2 (en) | 2008-08-15 | 2017-07-28 | Nivalis Therapeutics Inc | New pyrrole inhibitors of S-nitrosoglutathion reductase as therapeutic agents |
| BR112012024114B1 (pt) | 2010-03-22 | 2021-02-09 | Idorsia Pharmaceuticals Ltd | Compostos derivados de 3-(heteroarilamino)-1,2,3,4-tetrahidro-9h-carbazol, uso dos mesmos, e, composição farmacêutica |
| EP2457900A1 (fr) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | Nouveaux dérivés de pyrazole présentant un comportement antagoniste CRTH2 |
| MX2013007295A (es) * | 2010-12-23 | 2013-08-26 | Merck Sharp & Dohme | Quinoxalinas y aza-quinoxalinas como moduladores del receptor de crth2. |
| WO2012087872A1 (fr) | 2010-12-23 | 2012-06-28 | Merck Sharp & Dohme Corp. | Quinoléines et aza-quinoléines en tant que modulateurs de l'activité du récepteur crth2 |
| AU2012241442B2 (en) | 2011-04-14 | 2017-01-12 | Idorsia Pharmaceuticals Ltd | 7-(heteroaryl-amino)-6,7,8,9-tetrahydropyrido(1,2-a)indol acetic acid derivatives and their use as prostaglandin D2 receptor modulators |
| EP2545964A1 (fr) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Nouveaux composés se liant au fxr (nr1 h4) et modulant son activité |
| WO2013061977A1 (fr) | 2011-10-25 | 2013-05-02 | 塩野義製薬株式会社 | Dérivé hétérocyclique ayant une activité antagoniste des récepteurs à la pgd2 |
| MX2014007239A (es) | 2011-12-16 | 2014-08-08 | Atopix Therapeutics Ltd | Combinacion de un antagonista crth2 y un inhibidor de bomba de proton para el tratamiento de esofagitis eosinofilica. |
| LT3119779T (lt) | 2014-03-17 | 2018-09-10 | Idorsia Pharmaceuticals Ltd | Azaindolo acto rūgšties dariniai ir jų panaudojimas kaip prostaglandino d2 receptoriaus moduliatorių |
| TW201620909A (zh) | 2014-03-18 | 2016-06-16 | 艾克泰聯製藥有限公司 | 氮雜吲哚乙酸衍生物及彼等作為前列腺素ｄ２受體調節劑之用途 |
| WO2016020288A1 (fr) | 2014-08-04 | 2016-02-11 | Nuevolution A/S | Dérivés de pyrimidine substitués par un hétérocyclyle éventuellement condensés utiles pour le traitement des maladies inflammatoires, métaboliques, oncologiques et auto-immunes |
| US11091806B2 (en) | 2015-07-23 | 2021-08-17 | Merck Sharp & Dohme Corp. | Genetic markers associated with response to CRTH2 receptor antagonists |
| MX2018003202A (es) | 2015-09-15 | 2018-06-08 | Idorsia Pharmaceuticals Ltd | Formas cristalinas. |
| AU2016328150B2 (en) | 2015-09-23 | 2020-10-01 | Xw Laboratories Inc. | Prodrugs of gamma-hydroxybutyric acid, compositions and uses thereof |
| ES2805307T3 (es) * | 2015-09-29 | 2021-02-11 | Novartis Ag | Procedimiento para preparar ácido 1-(4-metanosulfonil-2-trifluorometil-bencil)-2-metil-1H-pirrolo[2,3-b]piridin-3-il-acético |
| WO2017210261A1 (fr) * | 2016-05-31 | 2017-12-07 | Concert Pharmaceuticals, Inc. | Févipiprant deutéré |
| PL3730487T3 (pl) | 2016-06-13 | 2022-08-16 | Gilead Sciences, Inc. | Pochodne azetydyny jako modulatory fxr (nr1h4) |
| CA2968836A1 (fr) | 2016-06-13 | 2017-12-13 | Gilead Sciences, Inc. | Composes modulant fxr (nr1h4) |
| CN106188040B (zh) * | 2016-06-28 | 2018-03-23 | 浙江宏鑫染化材料有限公司 | 一种Fevipiprant及其中间体的制备方法 |
| EP3489235A4 (fr) | 2016-07-21 | 2020-01-08 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Composé tricyclique en tant qu'inhibiteur de crth2 |
| JP6906626B2 (ja) | 2017-03-28 | 2021-07-21 | ギリアード サイエンシーズ， インコーポレイテッド | 肝疾患を処置するための治療的組み合わせ |
| KR102378845B1 (ko) | 2017-03-30 | 2022-03-24 | 엑스더블유파마 리미티드 | 이환형 헤테로아릴 유도체 및 이의 제조 및 용도 |
| JOP20190223A1 (ar) * | 2017-04-01 | 2019-09-26 | Novartis Ag | عملية لتحضير حمض 1-(4- ميثان سلفونيل -2- تراي فلورو ميثيل - بنزيل)-2- ميثيل -1h- بيرولو [2، 3-b] بيريدين -3- يل- أسيتيك |
| EP3644989A4 (fr) | 2017-06-30 | 2021-07-14 | The Regents of the University of California | Compositions et procédés de modulation de la pousse des cheveux |
| WO2019011336A1 (fr) * | 2017-07-14 | 2019-01-17 | 苏州科睿思制药有限公司 | Forme cristalline de qaw-039, son procédé de préparation et son utilisation |
| WO2019130166A1 (fr) * | 2017-12-26 | 2019-07-04 | Mankind Pharma Ltd. | Préparation de l'acide 2-[2-méthyl-1-[[4-méthylsulfonyl-2-(trifluoro méthyl)phényl]méthyl] pyrrolo[2,3-b]pyridin-3-yl]acétique |
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| CN110467612B (zh) * | 2018-05-09 | 2020-09-25 | 新发药业有限公司 | 一种前列腺素d2受体抑制剂化合物的简便制备方法 |
| EP3856719B1 (fr) | 2018-09-30 | 2023-06-07 | XWPharma Ltd. | Composés en tant qu'antagonistes du récepteur 3 de l'histamine neuronale et leurs utilisations |
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| JP2022519906A (ja) | 2019-02-19 | 2022-03-25 | ギリアード サイエンシーズ， インコーポレイテッド | Ｆｘｒアゴニストの固体形態 |
| TW202136194A (zh) | 2019-12-20 | 2021-10-01 | 香港商凱瑞康寧有限公司 | ４－纈胺醯氧基丁酸的合成方法 |
| EP4076657A1 (fr) | 2019-12-20 | 2022-10-26 | Nuevolution A/S | Composés actifs vis-à-vis des récepteurs nucléaires |
| MX2022012260A (es) | 2020-03-31 | 2022-11-30 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| CA3174176A1 (fr) | 2020-03-31 | 2021-10-07 | Sanne Schroder Glad | Composes actifs vis-a-vis des recepteurs nucleaires |
| US11357734B2 (en) | 2020-06-18 | 2022-06-14 | XWPharma Ltd. | Pharmaceutical granulations of water-soluble active pharmaceutical ingredients |
| CA3182394A1 (fr) | 2020-06-18 | 2021-12-23 | Sami Karaborni | Granulations d'administration controlee de principes actifs pharmaceutiques hydrosolubles |
| CN116261451A (zh) | 2020-07-24 | 2023-06-13 | 凯瑞康宁生物工程有限公司 | γ-羟基丁酸衍生物的药物组合物和药物动力学 |
| KR20230058151A (ko) | 2020-10-05 | 2023-05-02 | 엑스더블유파마 리미티드 | 감마-하이드록시부티르산 유도체의 변형된 방출 조성물 |
| AU2022238423A1 (en) | 2021-03-19 | 2023-10-19 | XWPharma Ltd. | Pharmacokinetics of combined release formulations of a gamma-hydroxybutyric acid derivative |
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| US3320268A (en) * | 1964-08-14 | 1967-05-16 | Merck & Co Inc | 1-aroyl or heteroaroyl-7-azaindole-3-carboxylates and derivatives |
| US5212195A (en) | 1992-05-13 | 1993-05-18 | Syntex (U.S.A.) Inc. | Substituted indole antagonists derivatives which are angiotensin II |
| GB9319297D0 (en) | 1993-09-17 | 1993-11-03 | Wellcome Found | Indole derivatives |
| EP0763035A4 (fr) | 1994-06-09 | 1997-10-01 | Smithkline Beecham Corp | Antagonistes du recepteur de l'endotheline |
| PL181895B1 (pl) | 1994-06-16 | 2001-10-31 | Pfizer | Nowe pirazolo-i pirolopirydyny _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ PL PL PL PL |
| TWI262920B (en) | 2000-10-27 | 2006-10-01 | Elbion Ag | New 7-azaindoles, their use as inhibitors of phosphodiesterase 4, and a method for synthesizing them |
| US7153852B2 (en) * | 2001-09-07 | 2006-12-26 | Ono Pharmaceutical Co., Ltd. | Indole compounds, process for producing the same and drugs containing the same as the active ingredient |
| SE0200356D0 (sv) * | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| WO2003097598A1 (fr) * | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Composé comprenant un antagonisme du récepteur de pdg2 |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| WO2005040112A1 (fr) | 2003-10-14 | 2005-05-06 | Oxagen Limited | Composes a activite antagoniste de pgd2 |
| GB0412914D0 (en) * | 2004-06-10 | 2004-07-14 | Oxagen Ltd | Compounds |
| MY144903A (en) * | 2004-06-17 | 2011-11-30 | Novartis Ag | Pyrrolopyridine derivatives and their use as crth2 antagonists |
| GB0525144D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525143D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525337D0 (en) * | 2005-12-13 | 2006-01-18 | Novartis Ag | Organic compounds |
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