RU2408587C2 - Производные пиримидинсульфонамида в качестве модуляторов рецепторов хемокинов - Google Patents
Производные пиримидинсульфонамида в качестве модуляторов рецепторов хемокинов Download PDFInfo
- Publication number
- RU2408587C2 RU2408587C2 RU2007106037/04A RU2007106037A RU2408587C2 RU 2408587 C2 RU2408587 C2 RU 2408587C2 RU 2007106037/04 A RU2007106037/04 A RU 2007106037/04A RU 2007106037 A RU2007106037 A RU 2007106037A RU 2408587 C2 RU2408587 C2 RU 2408587C2
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- Russia
- Prior art keywords
- alkyl
- group
- independently selected
- methyl
- thio
- Prior art date
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- 102000009410 Chemokine receptor Human genes 0.000 title 1
- 108050000299 Chemokine receptor Proteins 0.000 title 1
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims abstract 28
- 125000005842 heteroatom Chemical group 0.000 claims abstract 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 13
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000003814 drug Substances 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 5
- 239000001301 oxygen Substances 0.000 claims abstract 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- -1 hydroxy, amino Chemical group 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 108010018951 Interleukin-8B Receptors Proteins 0.000 claims abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 3
- 210000000440 neutrophil Anatomy 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract 2
- 208000001132 Osteoporosis Diseases 0.000 claims abstract 2
- 201000004681 Psoriasis Diseases 0.000 claims abstract 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract 2
- 208000006673 asthma Diseases 0.000 claims abstract 2
- 201000011510 cancer Diseases 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract 2
- 230000001404 mediated effect Effects 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 201000008482 osteoarthritis Diseases 0.000 claims abstract 2
- 102000005962 receptors Human genes 0.000 claims abstract 2
- 108020003175 receptors Proteins 0.000 claims abstract 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- UUTNJEMSGNMPIT-CYBMUJFWSA-N 5-(azetidine-1-carbonyl)-n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]furan-2-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)C(O1)=CC=C1C(=O)N1CCC1 UUTNJEMSGNMPIT-CYBMUJFWSA-N 0.000 claims 1
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 claims 1
- 229940124803 CXCR2 antagonist Drugs 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000002573 chemokine receptor CXCR2 antagonist Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- FMQAJAPZPDLOEL-UHFFFAOYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-(1,3-dihydroxy-2-methylpropan-2-yl)oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(OC(CO)(CO)C)=CC=1NS(=O)(=O)N1CCC1 FMQAJAPZPDLOEL-UHFFFAOYSA-N 0.000 claims 1
- BPZSEQWZOKOHSC-UHFFFAOYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-(1,3-dihydroxypropan-2-yloxy)pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(OC(CO)CO)=CC=1NS(=O)(=O)N1CCC1 BPZSEQWZOKOHSC-UHFFFAOYSA-N 0.000 claims 1
- LNUNDHAYWTUGQL-SNVBAGLBSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]-1,3-thiazole-2-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)C1=NC=CS1 LNUNDHAYWTUGQL-SNVBAGLBSA-N 0.000 claims 1
- MOAKFSKQBKCVTK-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]-1-methyl-6-oxopyridine-3-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)C=1C=CC(=O)N(C)C=1 MOAKFSKQBKCVTK-GFCCVEGCSA-N 0.000 claims 1
- JJOFKFQXYZWHHL-LLVKDONJSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]-1-methylimidazole-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)C1=CN(C)C=N1 JJOFKFQXYZWHHL-LLVKDONJSA-N 0.000 claims 1
- ITTVJRINDUYCJC-LLVKDONJSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCC1 ITTVJRINDUYCJC-LLVKDONJSA-N 0.000 claims 1
- FCVYGORXJJZDRI-SNVBAGLBSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]cyclopropanesulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)C1CC1 FCVYGORXJJZDRI-SNVBAGLBSA-N 0.000 claims 1
- VDTCBJYUZFBPEU-SECBINFHSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]methanesulfonamide Chemical compound OC[C@@H](C)OC1=CC(NS(C)(=O)=O)=NC(SCC=2C(=C(F)C=CC=2)F)=N1 VDTCBJYUZFBPEU-SECBINFHSA-N 0.000 claims 1
- DCDMRPOJLWYBFY-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]piperazine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCNCC1 DCDMRPOJLWYBFY-GFCCVEGCSA-N 0.000 claims 1
- KAPSQKJJSBQXPU-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]pyridine-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)C1=CC=NC=C1 KAPSQKJJSBQXPU-GFCCVEGCSA-N 0.000 claims 1
- DGQFZMVVCMJPPL-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r)-1-hydroxypropan-2-yl]oxypyrimidin-4-yl]pyrrolidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCCC1 DGQFZMVVCMJPPL-GFCCVEGCSA-N 0.000 claims 1
- QZECRCLSIGFCIO-BXUZGUMPSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r,3r)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@H](C)[C@H](O)CO)=CC=1NS(=O)(=O)N1CCC1 QZECRCLSIGFCIO-BXUZGUMPSA-N 0.000 claims 1
- VYBIXBYFWCLTPV-BXKDBHETSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r,3r)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]methanesulfonamide Chemical compound OC[C@@H](O)[C@@H](C)OC1=CC(NS(C)(=O)=O)=NC(SCC=2C(=C(F)C=CC=2)F)=N1 VYBIXBYFWCLTPV-BXKDBHETSA-N 0.000 claims 1
- RPZNTPKXYJJKJT-VXGBXAGGSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r,3r)-3-hydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@H](C)[C@H](O)C)=CC=1NS(=O)(=O)N1CCC1 RPZNTPKXYJJKJT-VXGBXAGGSA-N 0.000 claims 1
- QZECRCLSIGFCIO-RISCZKNCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r,3s)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@H](C)[C@@H](O)CO)=CC=1NS(=O)(=O)N1CCC1 QZECRCLSIGFCIO-RISCZKNCSA-N 0.000 claims 1
- OQQVPIXZKMQYTK-DOMZBBRYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r,3s)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]piperazine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@H](C)[C@@H](O)CO)=CC=1NS(=O)(=O)N1CCNCC1 OQQVPIXZKMQYTK-DOMZBBRYSA-N 0.000 claims 1
- STRBDUGJKNQVIH-LBPRGKRZSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2s)-2,3-dihydroxypropoxy]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(OC[C@@H](O)CO)=CC=1NS(=O)(=O)N1CCC1 STRBDUGJKNQVIH-LBPRGKRZSA-N 0.000 claims 1
- RPZNTPKXYJJKJT-RYUDHWBXSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2s,3s)-3-hydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@@H](C)[C@@H](O)C)=CC=1NS(=O)(=O)N1CCC1 RPZNTPKXYJJKJT-RYUDHWBXSA-N 0.000 claims 1
- ZIXYMRCGRAOYLM-UHFFFAOYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[3-hydroxy-2-(hydroxymethyl)propyl]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(CC(CO)CO)=CC=1NS(=O)(=O)N1CCC1 ZIXYMRCGRAOYLM-UHFFFAOYSA-N 0.000 claims 1
- TUHBMMWVWLMKNK-UHFFFAOYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-methoxypyrimidin-4-yl]-1-methylimidazole-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(OC)=CC=1NS(=O)(=O)C1=CN(C)C=N1 TUHBMMWVWLMKNK-UHFFFAOYSA-N 0.000 claims 1
- ZHWNAUARFIHHHI-UHFFFAOYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-methoxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(OC)=CC=1NS(=O)(=O)N1CCC1 ZHWNAUARFIHHHI-UHFFFAOYSA-N 0.000 claims 1
- KNPHDNZQXYLZMW-UHFFFAOYSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(OC)=CC=1NS(=O)(=O)N1CCNCC1 KNPHDNZQXYLZMW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000004429 atom Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 102000019034 Chemokines Human genes 0.000 abstract 1
- 108010012236 Chemokines Proteins 0.000 abstract 1
- 102000002791 Interleukin-8B Receptors Human genes 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 208000028774 intestinal disease Diseases 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- 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
- C07D405/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
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- A—HUMAN NECESSITIES
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| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| PT3263133T (pt) * | 2015-02-27 | 2020-05-21 | Univ Kyushu Nat Univ Corp | Composto de piridinona e a sua utilização |
| CN113893252A (zh) * | 2016-03-11 | 2022-01-07 | 阿迪亚生命科学公司 | 用于治疗结晶性关节病症的cxcr-2抑制剂 |
| US10660909B2 (en) | 2016-11-17 | 2020-05-26 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| WO2019165315A1 (en) | 2018-02-23 | 2019-08-29 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists alone or in combination |
| WO2023028077A1 (en) | 2021-08-24 | 2023-03-02 | Genentech, Inc. | Sodium channel inhibitors and methods of designing same |
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| RU2083567C1 (ru) * | 1991-04-25 | 1997-07-10 | Ф.Хоффманн-Ля Рош Аг | Производные арилсульфонамида или их соли и фармацевтическая композиция, проявляющая ангиопротекторное, антигипертензивное и вазоспазмолитическое, в частности противоишемическое, действие |
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| GB866843A (en) * | 1958-12-08 | 1961-05-03 | Ici Ltd | Sulphonamidopyrimidines |
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| US3452018A (en) * | 1966-08-29 | 1969-06-24 | American Home Prod | 1 - (2 - substituted - 6 - arylsulfonamidopyrimidin - 4 - yl)pyridinium hydroxide inner salts |
| US3673184A (en) * | 1970-09-02 | 1972-06-27 | Dainippon Pharmaceutical Co | Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives |
| JPS61118372A (ja) | 1984-11-12 | 1986-06-05 | Nippon Mektron Ltd | 新規ピリミジン誘導体およびその製造法 |
| JPS6442295A (en) | 1987-08-10 | 1989-02-14 | Seiko Epson Corp | Memory card mounting structure |
| JPH03197467A (ja) | 1989-12-26 | 1991-08-28 | Nippon Kayaku Co Ltd | ピリミジノン誘導体その製法及びそれを有効成分とする殺虫・殺ダニ剤 |
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2005
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- 2005-08-23 DK DK05773278.6T patent/DK1809624T3/da active
- 2005-08-23 PT PT5773278T patent/PT1809624E/pt unknown
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- 2005-08-23 CA CA2578441A patent/CA2578441C/en not_active Expired - Lifetime
- 2005-08-23 MX MX2007002240A patent/MX2007002240A/es active IP Right Grant
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2012
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