ZA200508722B - Pyrimidine derivatives useful for the treatment of diseases mediated by CRTH2 - Google Patents
Pyrimidine derivatives useful for the treatment of diseases mediated by CRTH2 Download PDFInfo
- Publication number
- ZA200508722B ZA200508722B ZA200508722A ZA200508722A ZA200508722B ZA 200508722 B ZA200508722 B ZA 200508722B ZA 200508722 A ZA200508722 A ZA 200508722A ZA 200508722 A ZA200508722 A ZA 200508722A ZA 200508722 B ZA200508722 B ZA 200508722B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzyl
- amino
- acetic acid
- dimethylamino
- chloro
- Prior art date
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- 150000003230 pyrimidines Chemical class 0.000 title claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 24
- 102000009389 Prostaglandin D receptors Human genes 0.000 title claims description 18
- 108050000258 Prostaglandin D receptors Proteins 0.000 title claims description 18
- 201000010099 disease Diseases 0.000 title claims description 16
- 238000011282 treatment Methods 0.000 title claims description 11
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
- 230000001404 mediated effect Effects 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
- -1 nitro, guanidino, pyrrolyl Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 25
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims description 5
- 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 201000009890 sinusitis Diseases 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 4
- 208000016557 Acute basophilic leukemia Diseases 0.000 claims description 4
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 4
- 206010052568 Urticaria chronic Diseases 0.000 claims description 4
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 4
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 4
- 208000024376 chronic urticaria Diseases 0.000 claims description 4
- 206010024378 leukocytosis Diseases 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- ZNTGLJGJOQBPOJ-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(2-cyclohexylacetyl)amino]phenyl]methyl]-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)CC3CCCCC3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 ZNTGLJGJOQBPOJ-UHFFFAOYSA-N 0.000 claims description 2
- CUNNBJJEJUDKNN-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 CUNNBJJEJUDKNN-UHFFFAOYSA-N 0.000 claims description 2
- OVWALNLURHWQRX-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(quinoline-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3N=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 OVWALNLURHWQRX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 15
- 239000003814 drug Substances 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- NRRCYZPJUABYHL-UHFFFAOYSA-N 2-Pyrimidine Acetic Acid Chemical class OC(=O)CC1=NC=CC=N1 NRRCYZPJUABYHL-UHFFFAOYSA-N 0.000 claims 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- QLEXLARZQWPJAH-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-fluorophenyl)methoxycarbonylamino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC(F)=CC=3)=CC=2)=N1 QLEXLARZQWPJAH-UHFFFAOYSA-N 0.000 claims 2
- UUEHKVXKFVUOKF-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(phenylmethoxycarbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC=CC=3)=CC=2)=N1 UUEHKVXKFVUOKF-UHFFFAOYSA-N 0.000 claims 2
- 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- BRAVLCWGFGRYAJ-UHFFFAOYSA-N 2-[2-[(4-benzamidophenyl)methyl]-4-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=CC=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BRAVLCWGFGRYAJ-UHFFFAOYSA-N 0.000 claims 1
- VNJYZANVNXLMBK-UHFFFAOYSA-N 2-[2-[1-[4-[(3,4-dichlorobenzoyl)amino]phenyl]ethyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound N=1C=C(CC(O)=O)C(N(C)C)=NC=1C(C)C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 VNJYZANVNXLMBK-UHFFFAOYSA-N 0.000 claims 1
- WFSKXLWLRRRIJO-UHFFFAOYSA-N 2-[2-[1-[4-[(4-chlorobenzoyl)amino]phenyl]ethyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound N=1C=C(CC(O)=O)C(N(C)C)=NC=1C(C)C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 WFSKXLWLRRRIJO-UHFFFAOYSA-N 0.000 claims 1
- AOUSMRYWAUOLEC-UHFFFAOYSA-N 2-[2-[[3-[(2-cyclopropylacetyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=1)=CC=CC=1NC(=O)CC1CC1 AOUSMRYWAUOLEC-UHFFFAOYSA-N 0.000 claims 1
- YSUZNPRBTKHJCF-UHFFFAOYSA-N 2-[2-[[3-[[2-(1,3-benzodioxol-5-yl)acetyl]amino]phenyl]methyl]-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=C(NC(=O)CC=3C=C4OCOC4=CC=3)C=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 YSUZNPRBTKHJCF-UHFFFAOYSA-N 0.000 claims 1
- AVTWECVCWPNYJR-UHFFFAOYSA-N 2-[2-[[3-[[benzyl(methyl)carbamoyl]amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=C(NC(=O)N(C)CC=3C=CC=CC=3)C=CC=2)=N1 AVTWECVCWPNYJR-UHFFFAOYSA-N 0.000 claims 1
- OQGHYGCQIHVPKX-UHFFFAOYSA-N 2-[2-[[4-(3,3-dimethylbutanoylamino)phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(NC(=O)CC(C)(C)C)=CC=C1CC1=NC=C(CC(O)=O)C(N2CCCC2)=N1 OQGHYGCQIHVPKX-UHFFFAOYSA-N 0.000 claims 1
- QWKZLHMASPOSDC-UHFFFAOYSA-N 2-[2-[[4-(benzylcarbamoylamino)phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)NCC=3C=CC=CC=3)=CC=2)=N1 QWKZLHMASPOSDC-UHFFFAOYSA-N 0.000 claims 1
- VIACNMLRKMDHEV-UHFFFAOYSA-N 2-[2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC1=CN=C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)N=C1N1CCCC1 VIACNMLRKMDHEV-UHFFFAOYSA-N 0.000 claims 1
- BLGFEKQGRRINTG-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4,6-bis(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C(Cl)=CC=3)=CC=2)=N1 BLGFEKQGRRINTG-UHFFFAOYSA-N 0.000 claims 1
- ZLEDKTARFAGUKH-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 ZLEDKTARFAGUKH-UHFFFAOYSA-N 0.000 claims 1
- WULJEVKZTZYJFW-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C(Cl)=CC=3)=CC=2)=N1 WULJEVKZTZYJFW-UHFFFAOYSA-N 0.000 claims 1
- OXZAIUCHPIZYDI-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-methyl-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 OXZAIUCHPIZYDI-UHFFFAOYSA-N 0.000 claims 1
- QBCSHZVZVUKCQO-UHFFFAOYSA-N 2-[2-[[4-[(4-acetamidobenzoyl)amino]phenyl]methyl]-4-chloro-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 QBCSHZVZVUKCQO-UHFFFAOYSA-N 0.000 claims 1
- AARBEQQNTOZBTL-UHFFFAOYSA-N 2-[2-[[4-[(4-bromobenzoyl)amino]phenyl]methyl]-4-chloro-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Br)=CC=3)=CC=2)=N1 AARBEQQNTOZBTL-UHFFFAOYSA-N 0.000 claims 1
- NGQGKGLUXQOOTE-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)-6-morpholin-4-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCOCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 NGQGKGLUXQOOTE-UHFFFAOYSA-N 0.000 claims 1
- LACBHKONDFDLLO-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=N1 LACBHKONDFDLLO-UHFFFAOYSA-N 0.000 claims 1
- YTMBTJPYTXLXLT-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 YTMBTJPYTXLXLT-UHFFFAOYSA-N 0.000 claims 1
- PTVJXKKBDDFIEH-UHFFFAOYSA-N 2-[2-[[4-[(4-fluorobenzoyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1 PTVJXKKBDDFIEH-UHFFFAOYSA-N 0.000 claims 1
- VIADXYASLLIBBI-NTEUORMPSA-N 2-[2-[[4-[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]phenyl]methyl]-4,6-bis(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)\C=C\C=3C=CC(Cl)=CC=3)=CC=2)=N1 VIADXYASLLIBBI-NTEUORMPSA-N 0.000 claims 1
- FLVDJNIFQHPSAB-KPKJPENVSA-N 2-[2-[[4-[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)\C=C\C=3C=CC(Cl)=CC=3)=CC=2)=N1 FLVDJNIFQHPSAB-KPKJPENVSA-N 0.000 claims 1
- NRDKCQHKFLCXRT-UHFFFAOYSA-N 2-[2-[[4-[[benzyl(methyl)carbamoyl]amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)N(C)CC=3C=CC=CC=3)=CC=2)=N1 NRDKCQHKFLCXRT-UHFFFAOYSA-N 0.000 claims 1
- HRFIBVDUAZPDBR-UHFFFAOYSA-N 2-[4,6-bis(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 HRFIBVDUAZPDBR-UHFFFAOYSA-N 0.000 claims 1
- JBCJIXHGOBOQOI-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[1-[4-(quinoline-2-carbonylamino)phenyl]ethyl]pyrimidin-5-yl]acetic acid Chemical compound C=1C=C(NC(=O)C=2N=C3C=CC=CC3=CC=2)C=CC=1C(C)C1=NC=C(CC(O)=O)C(N(C)C)=N1 JBCJIXHGOBOQOI-UHFFFAOYSA-N 0.000 claims 1
- HFENOWNHMIFNFE-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[1-[4-[(4-fluorobenzoyl)amino]phenyl]ethyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C=C(CC(O)=O)C(N(C)C)=NC=1C(C)C(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1 HFENOWNHMIFNFE-UHFFFAOYSA-N 0.000 claims 1
- WXBFZIGGWGVNCY-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-propan-2-ylpyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(C(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 WXBFZIGGWGVNCY-UHFFFAOYSA-N 0.000 claims 1
- VZQIUAMJIMFSOW-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC=1C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=1N1CCCC1 VZQIUAMJIMFSOW-UHFFFAOYSA-N 0.000 claims 1
- XSGQONMWVRQSTD-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 XSGQONMWVRQSTD-UHFFFAOYSA-N 0.000 claims 1
- SETQVYMZHIVBRU-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(phenylmethoxycarbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC=CC=3)=CC=2)=N1 SETQVYMZHIVBRU-UHFFFAOYSA-N 0.000 claims 1
- WZQHWHBFSVGSTJ-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(quinoline-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3N=C4C=CC=CC4=CC=3)=CC=2)=N1 WZQHWHBFSVGSTJ-UHFFFAOYSA-N 0.000 claims 1
- ZSKOFFLYTKCEIM-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(3-methoxybenzoyl)amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(CC=3N=C(C(CC(O)=O)=CN=3)N(C)C)=CC=2)=C1 ZSKOFFLYTKCEIM-UHFFFAOYSA-N 0.000 claims 1
- PBUBGDUPQPHGCQ-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(3-phenoxybenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 PBUBGDUPQPHGCQ-UHFFFAOYSA-N 0.000 claims 1
- ZQDSPCGDTTZJGO-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-fluorobenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1 ZQDSPCGDTTZJGO-UHFFFAOYSA-N 0.000 claims 1
- JQMMXIYSINFBCU-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 JQMMXIYSINFBCU-UHFFFAOYSA-N 0.000 claims 1
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- SBKQRLWONFKCFV-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-ethyl-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(CC)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 SBKQRLWONFKCFV-UHFFFAOYSA-N 0.000 claims 1
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- FZZZSCVAJSHOTP-UHFFFAOYSA-N 2-[4-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 FZZZSCVAJSHOTP-UHFFFAOYSA-N 0.000 claims 1
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- YGFDDDQXTSQSQN-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=C(Cl)N=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 YGFDDDQXTSQSQN-UHFFFAOYSA-N 0.000 claims 1
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- LAPHHRQYUAOFGX-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-chlorobenzoyl)-methylamino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(=CC=2)N(C)C(=O)C=2C=CC(Cl)=CC=2)=N1 LAPHHRQYUAOFGX-UHFFFAOYSA-N 0.000 claims 1
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- SLPMFCFFPOSDJT-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-methoxy-3,5-dimethylbenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=C(C)C(OC)=C(C)C=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 SLPMFCFFPOSDJT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
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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
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- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Immunology (AREA)
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- Dermatology (AREA)
- Otolaryngology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03009384A EP1471057B1 (en) | 2003-04-25 | 2003-04-25 | Pyrimidinylacetic acid derivatives useful for the treatment of diseases mediated by CRTH2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200508722B true ZA200508722B (en) | 2006-12-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200508722A ZA200508722B (en) | 2003-04-25 | 2004-04-14 | Pyrimidine derivatives useful for the treatment of diseases mediated by CRTH2 |
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Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| DK1471057T3 (da) | 2003-04-25 | 2006-05-15 | Actimis Pharmaceuticals Inc | Pyrimidinyleddikesyrederivater, der er egnede til behandlingen af sygdomme medieret af CRTH2 |
| SA04250253B1 (ar) * | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| ES2775204T3 (es) * | 2003-12-23 | 2020-07-24 | Genentech Inc | Nuevos anticuerpos anti IL13 y usos de los mismos |
| NZ548396A (en) | 2004-01-31 | 2010-06-25 | Actimis Pharmaceuticals Inc | Imidazo[1,2-C]pyrimidinylacetic acid derivatives |
| WO2005095397A1 (en) | 2004-03-11 | 2005-10-13 | Actelion Pharmaceuticals Ltd | Tetrahydropyridoindole derivatives |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| US8524715B2 (en) | 2004-11-23 | 2013-09-03 | Astrazeneca Ab | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| RU2453540C2 (ru) | 2005-04-21 | 2012-06-20 | Лаборатуар Сероно С.А. | 2,3-замещенные пиразинсульфонамиды в качестве ингибиторов crth2 |
| PT1891075E (pt) | 2005-05-24 | 2011-11-10 | Merck Serono Sa | Derivados espiro tricíclicos como moduladores do crth2 |
| DOP2006000210A (es) | 2005-10-04 | 2007-06-15 | Aventis Pharma Inc | Compuestos de pirimidina amida como inhibidores de pgds |
| EP1937632A1 (en) | 2005-10-06 | 2008-07-02 | Astra Zeneca AB | Novel compounds |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| WO2007062677A1 (en) * | 2005-11-30 | 2007-06-07 | 7Tm Pharma A/S | Thiazolyl- and pyrimidinyl-acetic acids and their use as crth2 receptor ligands |
| BRPI0712301A2 (pt) * | 2006-06-09 | 2012-01-17 | Icos Corp | composto, composição farmacêutica, método de antagonização de um receptor dp-2, e, uso de um composto |
| WO2008104869A1 (en) * | 2007-02-26 | 2008-09-04 | Pfizer Products Inc. | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| CN101772489B (zh) | 2007-06-21 | 2013-02-20 | 艾克提麦斯医药品有限公司 | 一种crth2拮抗剂的胺盐 |
| AU2008266853A1 (en) * | 2007-06-21 | 2008-12-24 | Actimis Pharmaceuticals, Inc. | Particulates of a CRTH2 antagonist |
| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| PT2205569E (pt) * | 2007-09-25 | 2012-05-25 | Actimis Pharmaceuticals Inc | Alquiltiopirimidinas como antagonistas de crth2 |
| KR20100061746A (ko) | 2007-09-25 | 2010-06-08 | 액티미스 파마수티컬스 인코포레이티드 | Ｃｒｔｈ２ 길항제로서의 ２－ｓ－벤질 치환된 피리미딘 |
| WO2009099902A1 (en) | 2008-02-01 | 2009-08-13 | Amira Pharmaceuticals, Inc. | N,n-disubstituted aminoalkylbiphenyl antagonists of prostaglandin d2 receptors |
| JP2011512359A (ja) | 2008-02-14 | 2011-04-21 | アミラ ファーマシューティカルズ，インク． | プロスタグランジンｄ２受容体のアンタゴニストとしての環式ジアリールエーテル化合物 |
| WO2009108720A2 (en) | 2008-02-25 | 2009-09-03 | Amira Pharmaceuticals, Inc. | Antagonists of prostaglandin d2 receptors |
| JP2011518130A (ja) | 2008-04-02 | 2011-06-23 | アミラ ファーマシューティカルズ，インク． | プロスタグランジンｄ２受容体のアミノアルキルフェニルアンタゴニスト |
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| EP2794563B1 (en) | 2011-12-21 | 2017-02-22 | Actelion Pharmaceuticals Ltd | Heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| WO2014006585A1 (en) | 2012-07-05 | 2014-01-09 | Actelion Pharmaceuticals Ltd | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| US20140148470A1 (en) * | 2012-11-23 | 2014-05-29 | Boehringer Ingelheim International Gmbh | Pyrimidine compounds for treating hairloss |
| TWI695831B (zh) | 2014-09-13 | 2020-06-11 | 香港商南北兄弟藥業投資有限公司 | Ｃｒｔｈ２拮抗劑化合物及其用途 |
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| BE790679A (fr) | 1971-11-03 | 1973-04-27 | Ici Ltd | Derives de l'indole |
| JPH03112985A (ja) * | 1989-09-28 | 1991-05-14 | Morishita Pharmaceut Co Ltd | Ｎ―（１ｈ―テトラゾール―５―イル）―２―フェニル―５―ピリミジンカルボキシアミド類及びその合成用中間体 |
| GB9125842D0 (en) | 1991-12-04 | 1992-02-05 | Ici Plc | Heterocyclic derivatives |
| US6326368B1 (en) * | 1996-03-27 | 2001-12-04 | Dupont Pharmaceuticals Company | Aryloxy- and arylthiosubstituted pyrimidines and triazines and derivatives thereof |
| CA2263198A1 (en) * | 1996-09-06 | 1998-03-12 | Nippon Kayaku Kabushiki Kaisha | Novel acetamide derivatives and protease inhibitors |
| JP2001302667A (ja) | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| AU2001260081B2 (en) * | 2000-05-22 | 2005-07-28 | Leo Pharma A/S | Benzophenones as inhibitors of il-1beta and tnf-alpha |
| US6878522B2 (en) * | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| SE0200411D0 (sv) * | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| EP1413306A1 (en) | 2002-10-21 | 2004-04-28 | Warner-Lambert Company LLC | Tetrahydroquinoline derivatives as CRTH2 antagonists |
| EP1585511B1 (en) | 2002-12-20 | 2013-01-23 | Amgen Inc. | Asthma and allergic inflammation modulators |
| DK1471057T3 (da) | 2003-04-25 | 2006-05-15 | Actimis Pharmaceuticals Inc | Pyrimidinyleddikesyrederivater, der er egnede til behandlingen af sygdomme medieret af CRTH2 |
| CN101772489B (zh) | 2007-06-21 | 2013-02-20 | 艾克提麦斯医药品有限公司 | 一种crth2拮抗剂的胺盐 |
| AU2008266853A1 (en) | 2007-06-21 | 2008-12-24 | Actimis Pharmaceuticals, Inc. | Particulates of a CRTH2 antagonist |
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