TWI353980B - Pyrimidine derivatives - Google Patents
Pyrimidine derivatives Download PDFInfo
- Publication number
- TWI353980B TWI353980B TW093111323A TW93111323A TWI353980B TW I353980 B TWI353980 B TW I353980B TW 093111323 A TW093111323 A TW 093111323A TW 93111323 A TW93111323 A TW 93111323A TW I353980 B TWI353980 B TW I353980B
- Authority
- TW
- Taiwan
- Prior art keywords
- amino
- group
- acetic acid
- benzyl
- alkyl
- Prior art date
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- 150000003230 pyrimidines Chemical class 0.000 title claims description 28
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 755
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 259
- -1 carboxy, decyl Chemical group 0.000 claims description 228
- 150000001875 compounds Chemical class 0.000 claims description 196
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 178
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 80
- 230000000694 effects Effects 0.000 claims description 61
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 59
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- 150000001412 amines Chemical class 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 238000007639 printing Methods 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 28
- 230000002079 cooperative effect Effects 0.000 claims description 27
- 239000007789 gas Substances 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 102000009389 Prostaglandin D receptors Human genes 0.000 claims description 24
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 150000003973 alkyl amines Chemical class 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 150000002825 nitriles Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 7
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 201000009890 sinusitis Diseases 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 5
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical group CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 claims description 5
- 208000016557 Acute basophilic leukemia Diseases 0.000 claims description 5
- 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims description 5
- 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims description 5
- 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 206010052568 Urticaria chronic Diseases 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 208000024376 chronic urticaria Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 235000003599 food sweetener Nutrition 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 239000003765 sweetening agent Substances 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- 201000003073 testicular leukemia Diseases 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 239000000052 vinegar Substances 0.000 claims description 2
- 235000021419 vinegar Nutrition 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 238000002347 injection Methods 0.000 claims 3
- 239000007924 injection Substances 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- HEEUMCHKVXTQIP-UHFFFAOYSA-N 2-pyrimidin-5-ylacetic acid Chemical compound OC(=O)CC1=CN=CN=C1 HEEUMCHKVXTQIP-UHFFFAOYSA-N 0.000 claims 2
- 206010011224 Cough Diseases 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 206010024378 leukocytosis Diseases 0.000 claims 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- NRRCYZPJUABYHL-UHFFFAOYSA-N 2-Pyrimidine Acetic Acid Chemical class OC(=O)CC1=NC=CC=N1 NRRCYZPJUABYHL-UHFFFAOYSA-N 0.000 claims 1
- LOCILIUQLADHQZ-UHFFFAOYSA-N 2-[2-[[4-[(3-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=C(Cl)C=CC=3)=CC=2)=N1 LOCILIUQLADHQZ-UHFFFAOYSA-N 0.000 claims 1
- BRLNZHPNOSUQCK-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(phenylcarbamoylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BRLNZHPNOSUQCK-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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- RYAQFHLUEMJOMF-UHFFFAOYSA-N 4-phenoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 RYAQFHLUEMJOMF-UHFFFAOYSA-N 0.000 claims 1
- WAGVAZQFCOMORW-UHFFFAOYSA-N 6-chloro-n,n-dimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC(Cl)=NC=N1 WAGVAZQFCOMORW-UHFFFAOYSA-N 0.000 claims 1
- 240000008564 Boehmeria nivea Species 0.000 claims 1
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- 208000003251 Pruritus Diseases 0.000 claims 1
- SYXNHFZRGOWGBG-UHFFFAOYSA-N benzoic acid;hexanoic acid Chemical compound CCCCCC(O)=O.OC(=O)C1=CC=CC=C1 SYXNHFZRGOWGBG-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D239/42—One nitrogen atom
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
- 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
-
- 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
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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 (2)
| Publication Number | Publication Date |
|---|---|
| TW200505873A TW200505873A (en) | 2005-02-16 |
| TWI353980B true TWI353980B (en) | 2011-12-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093111323A TWI353980B (en) | 2003-04-25 | 2004-04-23 | Pyrimidine derivatives |
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Families Citing this family (59)
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| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| DE60303238T2 (de) | 2003-04-25 | 2006-09-14 | Actimis Pharmaceuticals, Inc., La Jolla | Pyrimidin-Essigsäure Derivate geeignet zur Behandlung von CRTH2-bedingten Krankheiten |
| 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 |
| LT2805728T (lt) * | 2003-12-23 | 2020-05-25 | Genentech, Inc. | Nauji anti-il 13 antikūnai ir jų naudojimai |
| BRPI0507123A (pt) | 2004-01-31 | 2007-06-19 | Actimis Pharmaceuticals Inc | composto, medicamento, uso de um composto, e, processo para controlar um distúrbio ou doença associadas com a atividade de crth2 no ser humano e animais |
| BRPI0508540B8 (pt) | 2004-03-11 | 2021-05-25 | Actelion Pharmaceuticals Ltd | composto, composição farmacêutica, e, uso de um composto |
| 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 |
| KR101380448B1 (ko) | 2005-04-21 | 2014-04-11 | 메르크 세로노 에스. 에이. | ２，３치환된 피라진 술폰아미드 |
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| WO2007039736A1 (en) * | 2005-10-06 | 2007-04-12 | Astrazeneca 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 |
| AU2007256597A1 (en) * | 2006-06-09 | 2007-12-13 | Icos Corporation | Substituted phenyl acetic acids as DP-2 antagonists |
| CA2679198C (en) | 2007-02-26 | 2011-07-12 | Pfizer Products Inc. | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| MY149005A (en) * | 2007-06-21 | 2013-06-28 | Actimis Pharmaceuticals Inc | Amine salts of a crth2 antagonist |
| NZ581811A (en) * | 2007-06-21 | 2012-11-30 | Actimis Pharmaceuticals Inc | Particulates of the CRTH2 antagonist { 4,6-bis(dimethylamino)-2-(4-(4-(trifluoromethyl)benzamido)-benzyl)pyrimidin-5-yl} acetic acid |
| 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 |
| AR068633A1 (es) * | 2007-09-25 | 2009-11-25 | Actimis Pharmaceuticals Inc | Pirimidinas sustituidas con 2-s- bencilo como antagonistas de crth2 |
| US8168678B2 (en) | 2008-02-01 | 2012-05-01 | Panmira Pharmaceuticals, Inc. | N,N-disubstituted aminoalkylbiphenyl antagonists of prostaglandin D2 receptors |
| US8242145B2 (en) | 2008-02-14 | 2012-08-14 | Panmira Pharmaceuticals, Llc | Cyclic diaryl ether compounds as antagonists of prostaglandin D2 receptors |
| JP2011513242A (ja) | 2008-02-25 | 2011-04-28 | 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受容体アンタゴニスト |
| US8426449B2 (en) | 2008-04-02 | 2013-04-23 | Panmira Pharmaceuticals, Llc | Aminoalkylphenyl antagonists of prostaglandin D2 receptors |
| TWI403319B (zh) | 2008-07-03 | 2013-08-01 | Panmira Pharmaceuticals Llc | 前列腺素ｄ2受體之雜烷基拮抗劑 |
| EP2328876B1 (en) * | 2008-09-02 | 2012-11-21 | Actimis Pharmaceuticals, Inc., | Isotopically enriched pyrimidin-5-yl acetic acid derivatives as crth2 antagonists |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| WO2010039977A2 (en) | 2008-10-01 | 2010-04-08 | Amira Pharmaceuticals, Inc. | Heteroaryl antagonists of prostaglandin d2 receptors |
| US8524748B2 (en) | 2008-10-08 | 2013-09-03 | Panmira Pharmaceuticals, Llc | Heteroalkyl biphenyl antagonists of prostaglandin D2 receptors |
| GB2465062B (en) | 2008-11-06 | 2011-04-13 | Amira Pharmaceuticals Inc | Cycloalkane(B)azaindole antagonists of prostaglandin D2 receptors |
| WO2010057118A2 (en) | 2008-11-17 | 2010-05-20 | Amira Pharmaceuticals, Inc. | Heterocyclic antagonists of prostaglandin d2 receptors |
| KR20110098749A (ko) * | 2008-12-25 | 2011-09-01 | 다이쇼 세이야꾸 가부시끼가이샤 | 이소퀴놀린 유도체 |
| EP2393492A1 (en) * | 2009-02-09 | 2011-12-14 | Boehringer Ingelheim International GmbH | New pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| CA2751260A1 (en) | 2009-02-12 | 2010-08-19 | Stefano Crosignani | Phenoxy acetic acid derivatives |
| WO2010094643A1 (en) * | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| JP2013500978A (ja) | 2009-07-31 | 2013-01-10 | パンミラ ファーマシューティカルズ，エルエルシー． | Ｄｐ２受容体アンタゴニストの眼の医薬組成物 |
| MX2012001542A (es) | 2009-08-05 | 2012-06-19 | Panmira Pharmaceuticals Llc | Antagonista dp2 y usos del mismo. |
| GB0913636D0 (en) * | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| JP2013512242A (ja) * | 2009-11-24 | 2013-04-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ピリミジン−５−イル酢酸誘導体のコリン塩の多形体を調製する方法 |
| KR20120115989A (ko) | 2010-01-06 | 2012-10-19 | 판미라 파마슈티칼스, 엘엘씨 | Ｄｐ2 길항제 및 이의 용도 |
| SG182684A1 (en) | 2010-01-27 | 2012-08-30 | Boehringer Ingelheim Int | Pyrazole compounds as crth2 antagonists |
| SG186737A1 (en) | 2010-06-23 | 2013-02-28 | Taisho Pharmaceutical Co Ltd | Isoquinoline derivative |
| CA2805452C (en) | 2010-07-05 | 2018-07-31 | Actelion Pharmaceuticals Ltd | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| JP2013535457A (ja) | 2010-07-28 | 2013-09-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 呼吸器系及び炎症性疾患の治療用医薬組成物 |
| EP2598143A1 (en) | 2010-07-28 | 2013-06-05 | Boehringer Ingelheim International GmbH | Pharmaceutical compositions for treatment of respiratory and inflammatory diseases |
| CN102803407B (zh) | 2010-10-20 | 2016-11-16 | 威士伯采购公司 | 对包括铁素体不锈钢在内的宽范围的经涂布和未经涂布的基材具有改善粘附性的水基涂料体系 |
| MX2013005478A (es) | 2010-11-15 | 2013-08-29 | Univ Leuven Kath | Compuestos heterociclicos condensados antivirales. |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| TWI527809B (zh) | 2011-01-24 | 2016-04-01 | 百靈佳殷格翰國際股份有限公司 | 作為ｃｒｔｈ２拮抗劑之吡唑化合物 |
| EP2688882B1 (en) | 2011-03-25 | 2015-05-13 | Boehringer Ingelheim International GmbH | Pyrazole compounds as crth2 antagonists |
| DK2709988T3 (en) * | 2011-05-16 | 2017-09-18 | Actimis Pharmaceuticals Inc | METHOD FOR PREPARING [4,6-BIS-DIMETHYLAMINO-2- [4- (4-TRIFLUORMETHYLBENZOYL-AMINO) BENZYL] PYRIMIDIN-5-YL] ACETIC ACID |
| MX2014007239A (es) | 2011-12-16 | 2014-08-08 | Atopix Therapeutics Ltd | Combinacion de un antagonista crth2 y un inhibidor de bomba de proton para el tratamiento de esofagitis eosinofilica. |
| ES2624379T3 (es) | 2011-12-21 | 2017-07-14 | Idorsia Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor de prostaglandina D2 |
| JP6127135B2 (ja) | 2012-07-05 | 2017-05-10 | 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 | １−フェニル置換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 |
| 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 |
| RU2181360C2 (ru) * | 1996-09-06 | 2002-04-20 | Ниппон Каяку Кабусики Кайся | Новые производные ацетамида, способ их получения, фармацевтический состав и ингибиторы протеаз на их основе |
| 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 |
| CA2408727A1 (en) * | 2000-05-22 | 2001-11-29 | Leo Pharma A/S | Benzophenones as inhibitors of il-1.beta. 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 |
| DE60303238T2 (de) | 2003-04-25 | 2006-09-14 | Actimis Pharmaceuticals, Inc., La Jolla | Pyrimidin-Essigsäure Derivate geeignet zur Behandlung von CRTH2-bedingten Krankheiten |
| NZ581811A (en) | 2007-06-21 | 2012-11-30 | Actimis Pharmaceuticals Inc | Particulates of the CRTH2 antagonist { 4,6-bis(dimethylamino)-2-(4-(4-(trifluoromethyl)benzamido)-benzyl)pyrimidin-5-yl} acetic acid |
| MY149005A (en) | 2007-06-21 | 2013-06-28 | Actimis Pharmaceuticals Inc | Amine salts of a crth2 antagonist |
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