RU2006138603A - Антагонисты рецептора pgd2 для лечения воспалительных заболеваний - Google Patents
Антагонисты рецептора pgd2 для лечения воспалительных заболеваний Download PDFInfo
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- RU2006138603A RU2006138603A RU2006138603/04A RU2006138603A RU2006138603A RU 2006138603 A RU2006138603 A RU 2006138603A RU 2006138603/04 A RU2006138603/04 A RU 2006138603/04A RU 2006138603 A RU2006138603 A RU 2006138603A RU 2006138603 A RU2006138603 A RU 2006138603A
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- RU
- Russia
- Prior art keywords
- substituted
- methyl
- haloalkyl
- optionally substituted
- chlorophenyl
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- 208000027866 inflammatory disease Diseases 0.000 title claims 7
- 102000009389 Prostaglandin D receptors Human genes 0.000 title 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- -1 N- substituted nitrogen Chemical class 0.000 claims 275
- 125000001188 haloalkyl group Chemical group 0.000 claims 89
- 125000000217 alkyl group Chemical group 0.000 claims 59
- 150000001875 compounds Chemical class 0.000 claims 53
- 229910052736 halogen Inorganic materials 0.000 claims 51
- 150000002367 halogens Chemical class 0.000 claims 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims 40
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 38
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 32
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 30
- 125000004432 carbon atom Chemical group C* 0.000 claims 25
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 125000004076 pyridyl group Chemical group 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 19
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 238000000034 method Methods 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 19
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000002757 morpholinyl group Chemical group 0.000 claims 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- 125000002947 alkylene group Chemical group 0.000 claims 15
- 150000001412 amines Chemical class 0.000 claims 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000004193 piperazinyl group Chemical group 0.000 claims 12
- 125000003386 piperidinyl group Chemical group 0.000 claims 12
- 150000003278 haem Chemical class 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000002883 imidazolyl group Chemical group 0.000 claims 10
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 9
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 9
- 150000003973 alkyl amines Chemical class 0.000 claims 8
- 125000005265 dialkylamine group Chemical group 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 239000011737 fluorine Substances 0.000 claims 8
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 239000010802 sludge Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 7
- 125000001425 triazolyl group Chemical group 0.000 claims 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000006413 ring segment Chemical group 0.000 claims 6
- 150000001413 amino acids Chemical class 0.000 claims 5
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 239000007858 starting material Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
- 125000005879 dioxolanyl group Chemical group 0.000 claims 4
- 150000004820 halides Chemical group 0.000 claims 4
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 3
- 230000009435 amidation Effects 0.000 claims 3
- 238000007112 amidation reaction Methods 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 3
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims 3
- GVZYNAKETPFKJX-GTYOFVGBSA-N n-[(2s,4r)-1-[4-(1-acetylpiperidin-4-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@@H](C)C[C@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1CCN(C(C)=O)CC1 GVZYNAKETPFKJX-GTYOFVGBSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000006241 alcohol protecting group Chemical group 0.000 claims 2
- 201000009961 allergic asthma Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 125000000532 dioxanyl group Chemical group 0.000 claims 2
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- GVZYNAKETPFKJX-IPBJYNAHSA-N n-[(2r,4s)-1-[4-(1-acetylpiperidin-4-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@H](C)C[C@@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1CCN(C(C)=O)CC1 GVZYNAKETPFKJX-IPBJYNAHSA-N 0.000 claims 2
- AFAMKVNLVFKPFJ-RBISFHTESA-N n-[(2s,4r)-2-methyl-1-(4-morpholin-4-ylbenzoyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@@H](C)C[C@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1N1CCOCC1 AFAMKVNLVFKPFJ-RBISFHTESA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- MYNJXBPKZIIXFQ-SEODVWCLSA-N (e)-4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2-methylbut-2-enoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OC\C=C(/C)C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 MYNJXBPKZIIXFQ-SEODVWCLSA-N 0.000 claims 1
- IKFWMKOHWYZDQL-TVLSLMGLSA-N (e)-4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]but-2-enoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OC\C=C\C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 IKFWMKOHWYZDQL-TVLSLMGLSA-N 0.000 claims 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
- ADBZIZGMAVRJPN-UHFFFAOYSA-N 1,2,5-thiadiazolidine 1,1-dioxide Chemical compound O=S1(=O)NCCN1 ADBZIZGMAVRJPN-UHFFFAOYSA-N 0.000 claims 1
- XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 claims 1
- YOFFHWXQNYMXFJ-WTYVLRPYSA-N 2-[1-[[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]methyl]cyclopropyl]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC2(CC(O)=O)CC2)=CC=1)C)C1=CC=C(Cl)C=C1 YOFFHWXQNYMXFJ-WTYVLRPYSA-N 0.000 claims 1
- QYSLCJRJTURRSH-CQDCDSLLSA-N 2-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanoic acid Chemical compound C1=CC(OC(CC)C(O)=O)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C QYSLCJRJTURRSH-CQDCDSLLSA-N 0.000 claims 1
- MYXKEWUDEMSZSY-AVRWGWEMSA-N 2-[4-[(2s,4r)-4-(n-acetylanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]anilino]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(NCC(O)=O)=CC=1)C)C1=CC=CC=C1 MYXKEWUDEMSZSY-AVRWGWEMSA-N 0.000 claims 1
- DDUFMGXTZYMTAG-KCWXNJEJSA-N 2-[4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]piperazin-1-yl]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)N1CCN(CC(O)=O)CC1)C)C1=CC=C(Cl)C=C1 DDUFMGXTZYMTAG-KCWXNJEJSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- MHKWOVKKERULHT-UZTOHYMASA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylpropanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC(C)(C)C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 MHKWOVKKERULHT-UZTOHYMASA-N 0.000 claims 1
- IBTYRMFHNAPPFG-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]propanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 IBTYRMFHNAPPFG-HFJWLAOPSA-N 0.000 claims 1
- YZWCZPGTCFVCGQ-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]prop-2-enoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(C=CC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 YZWCZPGTCFVCGQ-HFJWLAOPSA-N 0.000 claims 1
- NNVFFZXAXQPCAQ-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]propanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(CCC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 NNVFFZXAXQPCAQ-HFJWLAOPSA-N 0.000 claims 1
- SAQMCTQCHVYQHD-MRDQGFSESA-N 3-[5-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]benzotriazol-1-yl]propanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C2N=NN(CCC(O)=O)C2=CC=1)C)C1=CC=C(Cl)C=C1 SAQMCTQCHVYQHD-MRDQGFSESA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- KIIZKTUGCNEFSQ-WTYVLRPYSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylbutanamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(C)(C)C(N)=O)=CC=1)C)C1=CC=C(Cl)C=C1 KIIZKTUGCNEFSQ-WTYVLRPYSA-N 0.000 claims 1
- WWHXNUCBACSWGB-WTYVLRPYSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylbutanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(C)(C)C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 WWHXNUCBACSWGB-WTYVLRPYSA-N 0.000 claims 1
- NNLOAUIUNCBHDH-KCWXNJEJSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-n-ethylbutanamide Chemical compound C1=CC(OCCCC(=O)NCC)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C NNLOAUIUNCBHDH-KCWXNJEJSA-N 0.000 claims 1
- VGRUGLYHGHQEDV-UZTOHYMASA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-n-hydroxybutanamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(=O)NO)=CC=1)C)C1=CC=C(Cl)C=C1 VGRUGLYHGHQEDV-UZTOHYMASA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- WNWCNNXROLONSM-CCLHPLFOSA-N C(C)(C)N1N=NC2=C1C=CC(=C2)C(=O)N2[C@H](C[C@H](C1=CC=CC=C21)N(C(CC)=O)C2=CC=CC=C2)C Chemical compound C(C)(C)N1N=NC2=C1C=CC(=C2)C(=O)N2[C@H](C[C@H](C1=CC=CC=C21)N(C(CC)=O)C2=CC=CC=C2)C WNWCNNXROLONSM-CCLHPLFOSA-N 0.000 claims 1
- DDTAARRRBWNEGR-RBISFHTESA-N C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC(CCC1=CC=C(C=C1)Cl)=O)C)=O Chemical compound C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC(CCC1=CC=C(C=C1)Cl)=O)C)=O DDTAARRRBWNEGR-RBISFHTESA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- QDVGFLOWCALOLI-QXNWPYRLSA-N C1CN(CC)CCC1C1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(=O)CC)C=3C=CC=CC=3)C[C@@H]2C)C=C1 Chemical compound C1CN(CC)CCC1C1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(=O)CC)C=3C=CC=CC=3)C[C@@H]2C)C=C1 QDVGFLOWCALOLI-QXNWPYRLSA-N 0.000 claims 1
- DQDYWOUHGAWEIL-MHECFPHRSA-N CCC(=O)N([C@H]1C2=CC=CC=C2N(C(=O)C2=C3C=CC=CC3=NO2)[C@@H](C)C1)C1=CC=CC=C1 Chemical compound CCC(=O)N([C@H]1C2=CC=CC=C2N(C(=O)C2=C3C=CC=CC3=NO2)[C@@H](C)C1)C1=CC=CC=C1 DQDYWOUHGAWEIL-MHECFPHRSA-N 0.000 claims 1
- INXMSJNSWCLKBD-YADARESESA-N CCC(=O)N([C@H]1C2=CC=CC=C2N(C(=O)C=2C=C3OCCOC3=CC=2)[C@@H](C)C1)C1=CC=CC=C1 Chemical compound CCC(=O)N([C@H]1C2=CC=CC=C2N(C(=O)C=2C=C3OCCOC3=CC=2)[C@@H](C)C1)C1=CC=CC=C1 INXMSJNSWCLKBD-YADARESESA-N 0.000 claims 1
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- SVTXJDGNDJXXMB-RXFWQSSRSA-N n-[(2s,4r)-2-methyl-1-(4-methyl-2,3-dihydro-1,4-benzoxazine-7-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound CCC(=O)N([C@H]1C2=CC=CC=C2N(C(=O)C=2C=C3OCCN(C)C3=CC=2)[C@@H](C)C1)C1=CC=CC=C1 SVTXJDGNDJXXMB-RXFWQSSRSA-N 0.000 claims 1
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- 239000012279 sodium borohydride Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
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- Urology & Nephrology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56041004P | 2004-04-07 | 2004-04-07 | |
| US60/560,410 | 2004-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2006138603A true RU2006138603A (ru) | 2008-05-20 |
Family
ID=34965223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006138603/04A RU2006138603A (ru) | 2004-04-07 | 2005-04-07 | Антагонисты рецептора pgd2 для лечения воспалительных заболеваний |
Country Status (21)
| Country | Link |
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| EP (1) | EP1740547A1 (https=) |
| JP (1) | JP2007532555A (https=) |
| KR (1) | KR20070002085A (https=) |
| CN (1) | CN101018770A (https=) |
| AR (1) | AR048528A1 (https=) |
| AU (1) | AU2005233125A1 (https=) |
| BR (1) | BRPI0509668A (https=) |
| CA (1) | CA2561564A1 (https=) |
| CL (1) | CL2008000069A1 (https=) |
| CR (1) | CR8659A (https=) |
| EC (1) | ECSP066977A (https=) |
| IL (1) | IL178328A0 (https=) |
| MA (1) | MA28566B1 (https=) |
| MX (1) | MXPA06011540A (https=) |
| NO (1) | NO20065107L (https=) |
| RU (1) | RU2006138603A (https=) |
| TN (1) | TNSN06320A1 (https=) |
| TW (1) | TW200538127A (https=) |
| UA (1) | UA84749C2 (https=) |
| WO (1) | WO2005100321A1 (https=) |
| ZA (1) | ZA200608955B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| UA90706C2 (ru) | 2005-02-24 | 2010-05-25 | Милленниум Фармасьютикалз, Инк. | Антагонисты рецептора pgd2 для лечения воспалительных заболеваний |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| BRPI0614692A2 (pt) | 2005-07-29 | 2009-05-19 | Hoffmann La Roche | derivados de indol-3-il-carbonil-piperidina e piperazina |
| EP2037967B1 (en) | 2006-06-16 | 2016-12-07 | The Trustees Of The University Of Pennsylvania | Prostaglandin d2 receptor antagonists for treating androgenetic alopecia |
| JP2010501567A (ja) | 2006-08-24 | 2010-01-21 | ノバルティス アクチエンゲゼルシャフト | 代謝系、心血管系および他の障害の処置のためのステアロイル−ＣｏＡ不飽和化酵素（ＳＣＤ）阻害剤としての２−（ピラジン−２−イル）−チアゾールおよび２−（１Ｈ−ピラゾール−３−イル）チアゾール誘導体ならびに関連化合物 |
| JPWO2008029924A1 (ja) | 2006-09-08 | 2010-01-21 | 大日本住友製薬株式会社 | 環状アミノアルキルカルボキサミド誘導体 |
| KR20090053923A (ko) | 2006-09-22 | 2009-05-28 | 노파르티스 아게 | 헤테로시클릭 유기 화합물 |
| CN101595105B (zh) | 2006-12-20 | 2013-01-23 | 诺瓦提斯公司 | 作为scd抑制剂的2-取代的5元杂环化合物 |
| EP2199283A1 (en) | 2007-09-27 | 2010-06-23 | Kowa Company, Ltd. | Prophylactic and/or therapeutic agent for anemia, comprising tetrahydroquinoline compound as active ingredient |
| PT2229358E (pt) | 2007-12-14 | 2011-06-29 | Pulmagen Therapeutics Asthma Ltd | Indoles e sua utilização terapêutica |
| JP2011102241A (ja) * | 2008-03-04 | 2011-05-26 | Dainippon Sumitomo Pharma Co Ltd | 新規１−アミノカルボニルピペリジン誘導体 |
| KR101660059B1 (ko) | 2008-08-22 | 2016-09-26 | 박스알타 인코퍼레이티드 | 중합체 벤질 카르보네이트-유도체 |
| JP2011256110A (ja) * | 2008-09-30 | 2011-12-22 | Takeda Chem Ind Ltd | ヘキサヒドロピロロキノリンの製造法 |
| JP5572154B2 (ja) | 2009-03-31 | 2014-08-13 | 興和株式会社 | テトラヒドロキノリン化合物を有効成分とする貧血の予防及び／又は治療剤 |
| GB0919431D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| WO2011054851A1 (en) | 2009-11-05 | 2011-05-12 | Glaxosmithkline Llc | Novel process |
| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| PH12013502619A1 (en) | 2011-06-17 | 2014-02-17 | Merck Sharp & Dohme | Cycloalkyl-fused tetrahydroquinolines as crth2 receptor modulators |
| EP2790696A1 (en) | 2011-12-16 | 2014-10-22 | Atopix Therapeutics Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| JP6097765B2 (ja) | 2011-12-21 | 2017-03-15 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | ヘテロシクリル誘導体及びプロスタグランジンｄ２受容体調節剤としてのそれらの使用 |
| WO2014006585A1 (en) | 2012-07-05 | 2014-01-09 | Actelion Pharmaceuticals Ltd | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| ES2991300T3 (es) | 2015-02-13 | 2024-12-03 | Inserm Institut Nat De La Sante Et De Larecherche Medicale | Antagonistas de PTGDR-1 y/o PTGDR-2 para prevenir y/o tratar lupus eritematoso sistémico |
| ES2947824T3 (es) | 2015-07-30 | 2023-08-21 | Univ Pennsylvania | Alelos polimórficos de un solo nucleótido del gen DP-2 humano para la detección de la susceptibilidad a la inhibición del crecimiento del cabello por antagonistas de PGD2 |
| JOP20190105A1 (ar) * | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| CR20200553A (es) | 2018-04-18 | 2021-04-08 | Constellation Pharmaceuticals Inc | Moduladores de enzimas modificadoras de metilo, composiciones y usos de estos |
| CN120097995A (zh) | 2018-05-21 | 2025-06-06 | 星座制药公司 | 甲基修饰酶的调节剂、其组合物和用途 |
| WO2021016414A1 (en) | 2019-07-24 | 2021-01-28 | Constellation Pharmaceuticals, Inc. | Crystalline forms of 7-chloro-2-(4-(3-methoxyazetidin-1-yl)cyclohexyl)-2,4-dimethyl-n-((6-methyl-4-(methylthio)-2-oxo-1,2-dihydropyridin-3-yl)methyl)benzo[d][1,3]dioxole-5-carboxamide |
| CN113201316B (zh) * | 2021-04-25 | 2022-08-26 | 西南石油大学 | 温度/CO2/pH多重响应性乳化剂和乳状液及其应用 |
| CN116425623B (zh) * | 2023-04-10 | 2024-02-13 | 大连凯飞化学股份有限公司 | 一锅法合成3,5-二氯-4-甲基苯甲酸的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR200002839T2 (tr) * | 1998-03-31 | 2001-01-22 | Shionogi & Co., Ltd. | 5-Hidroksibenzo[b]tiofen-3-karboksilik asit türevlerinin hazırlanması. |
| ATE316957T1 (de) * | 2001-04-30 | 2006-02-15 | Pfizer Prod Inc | Verbindungen verwendbar als zwischenprodukte für 4-aminochinolinderivate |
| JP2003321471A (ja) * | 2002-04-30 | 2003-11-11 | Fuji Photo Film Co Ltd | ラクタム化合物及びその製造方法 |
| US20040053842A1 (en) * | 2002-07-02 | 2004-03-18 | Pfizer Inc. | Methods of treatment with CETP inhibitors and antihypertensive agents |
| AU2003277285B2 (en) * | 2002-10-04 | 2007-12-13 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| EP1556356B1 (en) * | 2002-10-21 | 2006-05-31 | Warner-Lambert Company LLC | Tetrahydroquinoline derivatives as crth2 antagonists |
| JPWO2004052863A1 (ja) * | 2002-12-06 | 2006-04-13 | 協和醗酵工業株式会社 | 抗炎症剤 |
| EP1435356A1 (en) * | 2003-01-06 | 2004-07-07 | Warner-Lambert Company LLC | Quinoline derivatives as CRTH2 antagonists |
-
2005
- 2005-04-07 AU AU2005233125A patent/AU2005233125A1/en not_active Withdrawn
- 2005-04-07 CN CNA200580018590XA patent/CN101018770A/zh active Pending
- 2005-04-07 JP JP2007507467A patent/JP2007532555A/ja active Pending
- 2005-04-07 KR KR1020067023323A patent/KR20070002085A/ko not_active Ceased
- 2005-04-07 UA UAA200611678A patent/UA84749C2/ru unknown
- 2005-04-07 CA CA002561564A patent/CA2561564A1/en not_active Abandoned
- 2005-04-07 EP EP05733968A patent/EP1740547A1/en not_active Withdrawn
- 2005-04-07 RU RU2006138603/04A patent/RU2006138603A/ru not_active Application Discontinuation
- 2005-04-07 MX MXPA06011540A patent/MXPA06011540A/es not_active Application Discontinuation
- 2005-04-07 BR BRPI0509668-5A patent/BRPI0509668A/pt not_active IP Right Cessation
- 2005-04-07 AR ARP050101369A patent/AR048528A1/es unknown
- 2005-04-07 TW TW094111008A patent/TW200538127A/zh unknown
- 2005-04-07 WO PCT/US2005/011643 patent/WO2005100321A1/en not_active Ceased
-
2006
- 2006-09-27 CR CR8659A patent/CR8659A/es not_active Application Discontinuation
- 2006-09-27 IL IL178328A patent/IL178328A0/en unknown
- 2006-10-06 TN TNP2006000320A patent/TNSN06320A1/en unknown
- 2006-10-27 ZA ZA200608955A patent/ZA200608955B/xx unknown
- 2006-11-02 MA MA29430A patent/MA28566B1/fr unknown
- 2006-11-06 NO NO20065107A patent/NO20065107L/no not_active Application Discontinuation
- 2006-11-08 EC EC2006006977A patent/ECSP066977A/es unknown
-
2008
- 2008-01-10 CL CL200800069A patent/CL2008000069A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CR8659A (es) | 2007-06-08 |
| CA2561564A1 (en) | 2005-10-27 |
| MA28566B1 (fr) | 2007-05-02 |
| TNSN06320A1 (en) | 2008-02-22 |
| JP2007532555A (ja) | 2007-11-15 |
| IL178328A0 (en) | 2007-02-11 |
| UA84749C2 (ru) | 2008-11-25 |
| MXPA06011540A (es) | 2007-01-26 |
| KR20070002085A (ko) | 2007-01-04 |
| ZA200608955B (en) | 2009-05-27 |
| AR048528A1 (es) | 2006-05-03 |
| CN101018770A (zh) | 2007-08-15 |
| AU2005233125A1 (en) | 2005-10-27 |
| NO20065107L (no) | 2006-12-01 |
| CL2008000069A1 (es) | 2008-05-16 |
| WO2005100321A1 (en) | 2005-10-27 |
| ECSP066977A (es) | 2006-12-29 |
| TW200538127A (en) | 2005-12-01 |
| EP1740547A1 (en) | 2007-01-10 |
| BRPI0509668A (pt) | 2007-10-09 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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