HRP20090654T1 - Derivati indol-1-il octene kiseline koji imaju aktivnost antagonista pgd2 - Google Patents
Derivati indol-1-il octene kiseline koji imaju aktivnost antagonista pgd2 Download PDFInfo
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- HRP20090654T1 HRP20090654T1 HR20090654T HRP20090654T HRP20090654T1 HR P20090654 T1 HRP20090654 T1 HR P20090654T1 HR 20090654 T HR20090654 T HR 20090654T HR P20090654 T HRP20090654 T HR P20090654T HR P20090654 T1 HRP20090654 T1 HR P20090654T1
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- alkyl
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- 239000005557 antagonist Substances 0.000 title claims 3
- 230000000694 effects Effects 0.000 title claims 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 6
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 claims abstract 5
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 claims abstract 5
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 claims abstract 5
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims abstract 5
- 201000010099 disease Diseases 0.000 claims abstract 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 4
- 230000001404 mediated effect Effects 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 208000010247 contact dermatitis Diseases 0.000 claims 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims 5
- 201000008937 atopic dermatitis Diseases 0.000 claims 5
- -1 ethyl diamine Chemical class 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 206010010741 Conjunctivitis Diseases 0.000 claims 3
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 206010012442 Dermatitis contact Diseases 0.000 claims 3
- 206010065563 Eosinophilic bronchitis Diseases 0.000 claims 3
- 208000004262 Food Hypersensitivity Diseases 0.000 claims 3
- 206010016946 Food allergy Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- 208000009388 Job Syndrome Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 3
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- 206010039094 Rhinitis perennial Diseases 0.000 claims 3
- 208000036284 Rhinitis seasonal Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 206010000496 acne Diseases 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 3
- 201000009961 allergic asthma Diseases 0.000 claims 3
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 3
- 201000010105 allergic rhinitis Diseases 0.000 claims 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
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- 235000020932 food allergy Nutrition 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 206010051040 hyper-IgE syndrome Diseases 0.000 claims 3
- 208000008585 mastocytosis Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
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- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 208000017022 seasonal allergic rhinitis Diseases 0.000 claims 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- 102100031111 Disintegrin and metalloproteinase domain-containing protein 17 Human genes 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 229950010765 pivalate Drugs 0.000 claims 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 2
- 230000000699 topical effect Effects 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims 1
- IUTVDYPXKTVFCV-UHFFFAOYSA-N 2-[3-[[1-(2,4-difluorophenyl)sulfonylpyrrol-2-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CN1S(=O)(=O)C1=CC=C(F)C=C1F IUTVDYPXKTVFCV-UHFFFAOYSA-N 0.000 claims 1
- YSVZRJDOEFUDEM-UHFFFAOYSA-N 2-[3-[[1-(benzenesulfonyl)pyrrol-2-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CN1S(=O)(=O)C1=CC=CC=C1 YSVZRJDOEFUDEM-UHFFFAOYSA-N 0.000 claims 1
- MJRWWKBEDIUYIV-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[1-(4-methylphenyl)sulfonylpyrrol-2-yl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CN1S(=O)(=O)C1=CC=C(C)C=C1 MJRWWKBEDIUYIV-UHFFFAOYSA-N 0.000 claims 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 claims 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 claims 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
- 108091007505 ADAM17 Proteins 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- IECPWNUMDGFDKC-UHFFFAOYSA-N Fusicsaeure Natural products C12C(O)CC3C(=C(CCC=C(C)C)C(O)=O)C(OC(C)=O)CC3(C)C1(C)CCC1C2(C)CCC(O)C1C IECPWNUMDGFDKC-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 108090000978 Interleukin-4 Proteins 0.000 claims 1
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- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 102000000536 PPAR gamma Human genes 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
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- 239000007983 Tris buffer Substances 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 229940072056 alginate Drugs 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 1
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- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 238000009175 antibody therapy Methods 0.000 claims 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
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- 229940124748 beta 2 agonist Drugs 0.000 claims 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 1
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- 229910052791 calcium Inorganic materials 0.000 claims 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 1
- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 claims 1
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- 230000016396 cytokine production Effects 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 229940075930 picrate Drugs 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 1
- KASDHRXLYQOAKZ-ZPSXYTITSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-ZPSXYTITSA-N 0.000 claims 1
- 229960005330 pimecrolimus Drugs 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229960004586 rosiglitazone Drugs 0.000 claims 1
- 229960004017 salmeterol Drugs 0.000 claims 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 229960001967 tacrolimus Drugs 0.000 claims 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 claims 1
- 229960005332 zileuton Drugs 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 102000009389 Prostaglandin D receptors Human genes 0.000 abstract 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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Abstract
Spoj opće formule (I): naznačen time što je R1 halo ili cijano; R2 je C1-C4 alkil; iR3 je fenil supstituiran sa jednim ili više supstituenata izabranih od C1-C6 alkil, halo ili -SOL2(C1-C6 alkil); ili njegova farmaceutski prihvatljiva soll, hidrat, otopina ili kompleks. Patent sadrži još 15 patentnih zahtjeva.
Claims (16)
1. Spoj opće formule (I):
[image]
naznačen time što je R1 halo ili cijano;
R2 je C1-C4 alkil; i
R3 je fenil supstituiran sa jednim ili više supstituenata izabranih od C1-C6 alkil, halo ili -SOL2(C1-C6 alkil);
ili njegova farmaceutski prihvatljiva soll, hidrat, otopina ili kompleks.
2. Spoj opće formule (II):
[image]
naznačen time što su R1, R2 i R3 kao što su definirani za opću formulu (I); i
R4 je C1-C6 alkil, aril, (CH2)mOC(=O)C1-C6alkil, (CH2)mN(R5)2, CH((CH2)mO(C=O)R6)2;
m je 1 ili 2;
R5 je vodik ili metil;
R6 je C1-C18 alkil;
ili njegova farmaceutski prihvatljiva sol, hidrat, otopina ili kompleks.
3. Sol spoja prema patentnom zahtjevu 1 ili 2, naznačena time što je to sol natrija, kalija, kalcija, aluminija, cinka, magnezija, amonijeva sol, holin, dietilamin, TRIS, dietanolamin, etanolamin, etil diamin, piperazin, acetat, trifluoroacetat, laktat, glukonat, citrat, tartrat, maleat, malat, pantotenat, adipat, alginat, aspartat, benzoat, butirat, diglukonat, ciklopentanat, glukoheptanat, glicerofosfat, oksalat, heptanoat, heksanoat, fumarat, nikotinat, pamoat, pektinat, 3-fenilpropionat, pikrat, pivalat, proprionat, tartrat, laktobionat, pivolat, kamforat, undekanoat i sukcinat sol, sol organskih sulfonskih kiselina kao što je metansulfonat, etansulfonat, 2-hidroksietan sulfonat, kamforsulfonat, 2-naftalensulfonat, benzensulfonat, p-klorobenzensulfonat i p-toluensulfonat sol; i soli neorganskih kiselina kao što je hidroklorid, hidrobromid, hidrojodid, sulfat, bisulfat, hemisulfat, tiocijanat, persulfat, sol fosforne kiseline ili sulfonske kiseline.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time što, nezavisno ili u kombinaciji, R1 je halo i R2 je metil ili etil.
5. Spoj prema patentnom zahtjevu 4, naznačen time što je R1 fluoro i R2 je metil.
6. Spoj prema patentnim zahtjevima 1 ili 2 naznačen time što je to spoj:
[3-(1-Benzensulfonil-1H-pirol-2-ilmetil)-5-fluoro-2-metil-indol-1-il]-octena kiselina;
{5-Fluoro-2-metil-3-[1-(toluen-4-sulfonil)-1H-pirol-2-ilmetil]-indol-1-il}-octena kiselina; ili
{3-[1-(2,4-Difluoro-benzensulfonil)-1H-pirol-2-ilmetil]-5-fluoro-2-metil-indol-1-il}-octena kiselina;
ili njihov C1-C6 alkil, aril, (CH2)mOC(=O)C1-C6alkil, (CH2)mN(R5)2 ili CH((CH2)mO(C=O)R6)2 ester, u kojem su R5 i R6 kao što su definirani u patentnom zahtjevu 2.
7. Postupak za pripremu spoja prema patentnom zahtjevu 1, naznačen time što sadrži hidrolizu spoja prema patentnom zahtjevu 2 sa bazom.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time što se koristi za primjenu u medicini.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time što se koristi za primjenu u liječenju ili prevenciji alergijske astme, perenijalnog alergijskog rinitisa, sezonskog alergijskog rinitisa, atopijskog dermatitisa, kontaktne hipersenzitivnosti (uključujući kontaktni dermatitis), konjunktivitisa, posebno alergijskog konjunktivitisa, eozinofilnog bronhitisa, alergija na hranu, eozinofilnog gastroenteritisa, inflamatorne bolesti crijeva, ulceroznog kolitisa i Crohn-ove bolesti, mastocitoze i također drugih PGD2-posredovanih bolesti, na primjer autoimunih bolesti kao što je hiper IgE sindrom i sistemski lupus eritematodes, psolrijaza, akne, multipla skleroza, odbacivanje alotransplanta, reperfuziona povreda, kronična opstruktivna bolest pluća, kao i reumatoidni artritis, psolrijatički artritis i osteoartritis i neurodegenerativne bolesti kao što su Alzheimer-ova bolest, Parkinsoln-ova bolest, šlog i amiotrofna lateralna skleroza.
10. Primjena spoja prema bilo kojem od patentnih zahtjeva 1 do 6, naznačena time što se koristi u pripremi sredstva za liječenje alergijske astme, perenijalnog alergijskog rinitisa, sezonskog alergijskog rinitisa, atopijskog dermatitisa, kontaktne hipersenzitivnosti (uključujući kontaktni dermatitis), konjunktivitisa, posebnoo alergijskog konjunktivitisa, eozinofilnog bronhitisa, alergija na hranu, eozinofilnog gastroenteritisa, inflamatorne bolesti crijeva, ulceroznog kolitisa i Crohn-ove bolesti, mastocitoze i također drugih PGD2-posredovanih bolesti, na primjer autoimunih bolesti kao što je hiper IgE sindrom i sistemski lupus eritematodes, psolrijaza, akne, multipla skleroza, odbacivanje alotransplanta, reperfuziona povreda, kronična opstruktivna bolest pluća, kao i reumatoidni artritis, psolrijatički artritis i osteoartritis i neurodegenerativne bolesti kao što su Alzheimer-ova bolest, Parkinsoln-ova bolest, šlog i amiotrofna lateralna skleroza.
11. Farmaceutska kompozicija naznačena time što sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 6 zajedno sa farmaceutskim inertnim puniteljem ili nosačem.
12. Farmaceutska kompozicija prema patentnom zahtjevu 11, naznačena time što se koristi za primjenu nazalnom, bukalnom ili topikalnom primjenom, uključujući topikalnu primjenu na oko.
13. Farmaceutska kompozicija prema patentnom zahtjevu 11 ili 12 naznačena time što dalje sadrži dodatno aktivno sredstvo.
14. Primjena prema patentnom zahtjevu 10, naznačena time što sredstvo također sadrži dodatno aktivno sredstvo.
15. Farmaceutska kompozicija prema patentnom zahtjevu 13 ili primjena prema patentnom zahtjevu 14, naznačena time što dodatno aktivno sredstvo sadrži:
β2 agoniste kao što je salmeterol;
kortikosteroide kao što je flutikazon;
antihistaminike kao što je loratidin;
antagoniste leukotriena kao što je montelukast;
terapije anti-IgE antitija kao što je omalizumab;
anti-infektivna sredstva kao što je fuzidinska kiselina (posebno za liječenje atopijskog dermatitisa);
sredstva protiv gljivica kao što je klotrimazol (posebno za liječenje atopijskog dermatitisa);
imunosupresante kao što je takrolimus i posebno o pimekrolimus u slučaju inflamatorne bolesti kože;
druge antagoniste PGD2 koji djeluju na drugim receptorima, kao što su antagonisti DP;
inhibitore fosfodiesteraze tip 4 kao što je cilonilast;
lijekove koji moduliraju proizvodnju citokina kao što su inhibitori TNFα konvertujućeg enzima (TACE);
lijekove koji moduliraju aktivnost Th2 citokina IL-4 i IL-5 kao što je blokiranje monoklonalnih antitijela i otopljivih receptora;
agoniste PPAR-γ kao što je rosiglitazon;
inhibitore 5-lipoksigenaze kao što je zileuton.
16. Proizvod naznačen time što sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 6 i jedno ili više sredstava navedenih u patentnom zahtjevu 15 kao kombinirani preparat za istovremenu, odvojenu ili uzastopnu primjenu u liječenju ili prevenciji alergijske astme, perenijalnog alergijskog rinitisa, sezonskog alergijskog rinitisa, atopijskog dermatitisa, kontaktne hipersenzitivnosti (uključujući kontaktni dermatitis), konjunktivitisa, posebno alergijskog konjunktivitisa, eozinofilnog bronhitisa, alergija na hranu, eozinofilnog gastroenteritisa, inflamatorne bolesti crijeva, ulceroznog kolitisa i Crohn-ove bolesti, mastocitoze i također drugih PGD2-posredovanih bolesti, na primjer autoimunih bolesti kao što je hiper IgE sindrom i sistemski lupus eritematodes, psolrijaza, akne, multipla skleroza, odbacivanje alotransplanta, reperfuziona povreda, kronična opstruktivna bolest pluća, kao i reumatoidni artritis, psolrijatički artritis i osteoartritis i neurodegenerativne bolesti kao što su Alzheimer-ova bolest, Parkinsoln-ova bolest, šlog i amiotrofna lateralna skleroza.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0505048.9A GB0505048D0 (en) | 2005-03-11 | 2005-03-11 | Compounds with PGD antagonist activity |
| PCT/GB2006/000851 WO2006095183A1 (en) | 2005-03-11 | 2006-03-10 | 1-acetic acid-indole derivatives with pgd2 antagonist activity |
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| Publication Number | Publication Date |
|---|---|
| HRP20090654T1 true HRP20090654T1 (hr) | 2010-01-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| HR20090654T HRP20090654T1 (hr) | 2005-03-11 | 2009-12-09 | Derivati indol-1-il octene kiseline koji imaju aktivnost antagonista pgd2 |
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| Country | Link |
|---|---|
| US (1) | US8044088B2 (hr) |
| EP (1) | EP1856045B1 (hr) |
| JP (1) | JP2008532990A (hr) |
| KR (1) | KR20070116633A (hr) |
| CN (1) | CN101166721A (hr) |
| AT (1) | ATE442356T1 (hr) |
| AU (1) | AU2006221784A1 (hr) |
| BR (1) | BRPI0608732A2 (hr) |
| CA (1) | CA2601980A1 (hr) |
| CY (1) | CY1109532T1 (hr) |
| DE (1) | DE602006009080D1 (hr) |
| DK (1) | DK1856045T3 (hr) |
| ES (1) | ES2333161T3 (hr) |
| GB (1) | GB0505048D0 (hr) |
| HK (1) | HK1109628A1 (hr) |
| HR (1) | HRP20090654T1 (hr) |
| IL (1) | IL185844A0 (hr) |
| MX (1) | MX2007011091A (hr) |
| NO (1) | NO20074641L (hr) |
| NZ (1) | NZ561747A (hr) |
| PL (1) | PL1856045T3 (hr) |
| PT (1) | PT1856045E (hr) |
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| SI (1) | SI1856045T1 (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| EP2037967B1 (en) | 2006-06-16 | 2016-12-07 | The Trustees Of The University Of Pennsylvania | Prostaglandin d2 receptor antagonists for treating androgenetic alopecia |
| KR20090042808A (ko) | 2006-07-22 | 2009-04-30 | 옥사겐 리미티드 | 씨알티에이치2 길항제 활성을 갖는 화합물 |
| NZ574705A (en) | 2006-08-07 | 2011-12-22 | Actelion Pharmaceuticals Ltd | (3-amino-1,2,3,4-tetrahydro-9h-carbazol-9-yl)-acetic acid derivatives |
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| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| SE0302232D0 (sv) * | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
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| SE0303180D0 (sv) | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
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| EP2240444A1 (en) * | 2008-01-22 | 2010-10-20 | Oxagen Limited | Compounds having crth2 antagonist activity |
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- 2006-03-10 KR KR1020077023379A patent/KR20070116633A/ko not_active Application Discontinuation
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| HK1109628A1 (en) | 2008-06-13 |
| JP2008532990A (ja) | 2008-08-21 |
| NO20074641L (no) | 2007-11-01 |
| DK1856045T3 (da) | 2010-01-04 |
| GB0505048D0 (en) | 2005-04-20 |
| SI1856045T1 (sl) | 2010-01-29 |
| BRPI0608732A2 (pt) | 2016-11-08 |
| ZA200708159B (en) | 2009-11-25 |
| KR20070116633A (ko) | 2007-12-10 |
| US8044088B2 (en) | 2011-10-25 |
| AU2006221784A1 (en) | 2006-09-14 |
| CN101166721A (zh) | 2008-04-23 |
| CA2601980A1 (en) | 2006-09-14 |
| ATE442356T1 (de) | 2009-09-15 |
| RU2007134456A (ru) | 2009-04-20 |
| NZ561747A (en) | 2010-03-26 |
| ES2333161T3 (es) | 2010-02-17 |
| DE602006009080D1 (de) | 2009-10-22 |
| RS51016B (sr) | 2010-10-31 |
| US20100330077A1 (en) | 2010-12-30 |
| EP1856045B1 (en) | 2009-09-09 |
| PT1856045E (pt) | 2009-12-09 |
| EP1856045A1 (en) | 2007-11-21 |
| MX2007011091A (es) | 2007-11-22 |
| CY1109532T1 (el) | 2014-08-13 |
| PL1856045T3 (pl) | 2010-02-26 |
| WO2006095183A1 (en) | 2006-09-14 |
| IL185844A0 (en) | 2008-01-06 |
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