AU2003233671B2 - Calcium receptor modulating arylalkylamines - Google Patents
Calcium receptor modulating arylalkylamines Download PDFInfo
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- AU2003233671B2 AU2003233671B2 AU2003233671A AU2003233671A AU2003233671B2 AU 2003233671 B2 AU2003233671 B2 AU 2003233671B2 AU 2003233671 A AU2003233671 A AU 2003233671A AU 2003233671 A AU2003233671 A AU 2003233671A AU 2003233671 B2 AU2003233671 B2 AU 2003233671B2
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- Prior art keywords
- methyl
- phenyl
- methyloxy
- ethanamine
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 102000013830 Calcium-Sensing Receptors Human genes 0.000 title 1
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 title 1
- 150000003975 aryl alkyl amines Chemical class 0.000 title 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 88
- -1 C 1 4alkoxy Chemical group 0.000 claims 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 55
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000001624 naphthyl group Chemical group 0.000 claims 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 31
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 27
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical group 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000001188 haloalkyl group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 125000004429 atom Chemical group 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 229910052717 sulfur Inorganic materials 0.000 claims 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 238000000034 method Methods 0.000 claims 10
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims 9
- 229920006395 saturated elastomer Chemical group 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 6
- 125000003944 tolyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 201000002980 Hyperparathyroidism Diseases 0.000 claims 4
- 208000001132 Osteoporosis Diseases 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- CJWGCBRQAHCVHW-UHFFFAOYSA-N 1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC(C(C)N)=C1 CJWGCBRQAHCVHW-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229960003966 nicotinamide Drugs 0.000 claims 3
- 239000011570 nicotinamide Substances 0.000 claims 3
- 230000028327 secretion Effects 0.000 claims 3
- 208000020084 Bone disease Diseases 0.000 claims 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
- TVCVZPPTRJJNOP-UHFFFAOYSA-N 1,2-dihydropyridine-2-carboxylic acid Chemical compound OC(=O)C1NC=CC=C1 TVCVZPPTRJJNOP-UHFFFAOYSA-N 0.000 claims 1
- QJXDHSSSGPGEQC-UHFFFAOYSA-N 1-(3-bromophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC=CC(Br)=C1 QJXDHSSSGPGEQC-UHFFFAOYSA-N 0.000 claims 1
- UZDDXUMOXKDXNE-UHFFFAOYSA-N 1-(4-methylphenyl)ethanamine Chemical compound CC(N)C1=CC=C(C)C=C1 UZDDXUMOXKDXNE-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- IYZIARNSXPGYSC-UHFFFAOYSA-N 3-phenylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 IYZIARNSXPGYSC-UHFFFAOYSA-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
- LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- YCNDLQRBCKYYFD-UHFFFAOYSA-N COC1=CC=CC(C(C)NCC=2C=C(C(OC)=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 Chemical compound COC1=CC=CC(C(C)NCC=2C=C(C(OC)=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 YCNDLQRBCKYYFD-UHFFFAOYSA-N 0.000 claims 1
- WAHHHNYICCZJFL-UHFFFAOYSA-N COC1=CC=CC(C(C)NCC=2C=C(C(OC)=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 Chemical compound COC1=CC=CC(C(C)NCC=2C=C(C(OC)=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 WAHHHNYICCZJFL-UHFFFAOYSA-N 0.000 claims 1
- BSFGFDBHPRSHLE-UHFFFAOYSA-N COC1=CC=CC(C(C)NCC=2C=C(C(OC)=CC=2)C=2SC=CC=2)=C1 Chemical compound COC1=CC=CC(C(C)NCC=2C=C(C(OC)=CC=2)C=2SC=CC=2)=C1 BSFGFDBHPRSHLE-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethanediamine Natural products NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910003827 NRaRb Inorganic materials 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- PDSIQAILYQYARH-GOSISDBHSA-N ethyl 4-[2-methoxy-5-[[[(1r)-1-(3-methoxyphenyl)ethyl]amino]methyl]phenyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC(CN[C@H](C)C=2C=C(OC)C=CC=2)=CC=C1OC PDSIQAILYQYARH-GOSISDBHSA-N 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000000286 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
- 239000004576 sand Substances 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Classifications
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- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
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- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
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- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
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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
- 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
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- 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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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| KR101020350B1 (ko) * | 2003-03-13 | 2011-03-08 | 이데미쓰 고산 가부시키가이샤 | 신규한 질소 함유 헤테로환 유도체 및 이를 이용한 유기 전기발광 소자 |
| WO2005065050A2 (ja) * | 2003-12-25 | 2005-07-21 | Asahi Kasei Pharma Corporation | ２環化合物 |
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| KR101182690B1 (ko) * | 2004-03-02 | 2012-09-14 | 아벤티스 파마슈티칼스 인크. | 트립타제 억제제의 제조방법 |
| PT1757582E (pt) | 2004-05-28 | 2016-03-04 | Mitsubishi Tanabe Pharma Corp | Arilalquilaminas e processo para a sua produção |
| US7361789B1 (en) | 2004-07-28 | 2008-04-22 | Amgen Inc. | Dihydronaphthalene compounds, compositions, uses thereof, and methods for synthesis |
| US20060276534A1 (en) * | 2005-03-17 | 2006-12-07 | Amgen Inc. | Methods of decreasing calcification |
| EP1882684B1 (en) * | 2005-05-19 | 2014-12-10 | Astellas Pharma Inc. | Pyrrolidine derivative or salt thereof |
| EP1904491A2 (en) * | 2005-05-31 | 2008-04-02 | Vertex Pharmaceuticals Incorporated | Heterocycles useful as modulators of ion channels |
| WO2007037795A2 (en) * | 2005-08-05 | 2007-04-05 | Amgen Inc. | Stable aqueous protein or antibody pharmaceutical formulations and their preparation |
| ES2400693T3 (es) * | 2005-09-02 | 2013-04-11 | Amgen Inc. | Regulación del equilibrio de fluido intestinal usando calcimiméticos |
| JP2009512710A (ja) * | 2005-10-21 | 2009-03-26 | アムジエン・インコーポレーテツド | Ｉｌ−１阻害剤を用いて血管石灰化を抑制する方法 |
| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
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| CA2648939C (en) * | 2006-04-20 | 2014-07-08 | Amgen Inc. | Stable emulsion formulations |
| GB0614579D0 (en) * | 2006-07-21 | 2006-08-30 | Black James Foundation | Pyrimidine derivatives |
| US20100222345A1 (en) * | 2006-08-09 | 2010-09-02 | Caroline Jean Diaz | Novel compounds as antagonists or inverse agonists for opioid receptors |
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| EP2079525A1 (en) * | 2006-10-26 | 2009-07-22 | Amgen Inc. | Calcium receptor modulating agents |
| KR20090064478A (ko) * | 2006-11-13 | 2009-06-18 | 화이자 프로덕츠 인크. | 디아릴, 디피리디닐 및 아릴-피리디닐 유도체, 및 이들의 용도 |
| TW200840566A (en) * | 2006-12-22 | 2008-10-16 | Esteve Labor Dr | Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments |
| US8093299B2 (en) | 2007-03-30 | 2012-01-10 | Amgen Inc. | Methods of treating bowel disorders |
| WO2009051718A2 (en) * | 2007-10-15 | 2009-04-23 | Amgen Inc. | Calcium receptor modulating agents |
| WO2009121015A2 (en) * | 2008-03-28 | 2009-10-01 | Amgen Inc. | Methods of treating epithelial injury |
| WO2010042642A1 (en) * | 2008-10-08 | 2010-04-15 | Amgen Inc. | Calcium receptor modulating agents |
| WO2010052448A2 (en) * | 2008-11-05 | 2010-05-14 | Ucb Pharma S.A. | Fused pyrazine derivatives as kinase inhibitors |
| WO2010104882A1 (en) | 2009-03-10 | 2010-09-16 | Amgen Inc. | Methods of modulating sperm motility |
| DE102009015697A1 (de) | 2009-03-31 | 2010-10-07 | Markus Dr. Heinrich | Verfahren zur Arylierung von ringsubstituierten Phenolen und Phenylethern |
| JP2012528086A (ja) | 2009-05-27 | 2012-11-12 | レオ ファーマ アクティーゼルスカブ | 新規のカルシウム感知受容体調節化合物およびその医薬用途 |
| WO2010136035A2 (en) | 2009-05-27 | 2010-12-02 | Leo Pharma A/S | Novel calcium sensing receptor modulating compounds and pharmaceutical use thereof |
| US9056814B2 (en) | 2010-06-30 | 2015-06-16 | Leo Pharma A/S | Polymorphic form of a calcimimetic compound |
| RU2599788C2 (ru) | 2010-06-30 | 2016-10-20 | Лео Фарма А/С | Новая полиморфная форма кальцимиметического соединения |
| EP2643292A1 (en) | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| EP2643291A2 (en) | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| JP2014500882A (ja) | 2010-11-26 | 2014-01-16 | レオ ファーマ アクティーゼルスカブ | カルシウム感知受容体活性化合物 |
| US20130261132A1 (en) | 2010-11-26 | 2013-10-03 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| AP2013007153A0 (en) * | 2011-03-18 | 2013-09-30 | Lupin Ltd | Benzo [B] [1,4] oxazin derivatives as calcium sensing receptor modulators |
| EP2888225A1 (en) * | 2012-08-27 | 2015-07-01 | Lupin Limited | Arylalkylamine compounds as calcium sensing receptor modulators |
| GB201217330D0 (en) | 2012-09-28 | 2012-11-14 | Univ Cardiff | Therapeutic for treating inflammatory lung disorders |
| CN104292157A (zh) * | 2014-09-15 | 2015-01-21 | 湖南华腾制药有限公司 | 一种1-(喹啉-4-基)乙胺的制备方法 |
| WO2017037616A1 (en) * | 2015-08-31 | 2017-03-09 | Lupin Limited | Arylalkylamine compounds as calcium sensing receptor modulators |
| DE102015011861B4 (de) | 2015-09-10 | 2018-03-01 | Rudolf Schindler | Neue cyclische Carboxamide als NMDA NR2B Rezeptor Inhibitoren |
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| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| WO1999048888A1 (en) * | 1998-03-25 | 1999-09-30 | Bristol-Myers Squibb Company | Imidazolone anorectic agents: ii. phenyl derivatives |
| WO2003020723A1 (en) * | 2001-08-30 | 2003-03-13 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-a]PYRIMIDINE DERIVATIVE |
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| JP2010150268A (ja) | 2010-07-08 |
| JP4486882B2 (ja) | 2010-06-23 |
| US20070142381A1 (en) | 2007-06-21 |
| EP1509497A1 (en) | 2005-03-02 |
| PL376438A1 (en) | 2005-12-27 |
| US20040082625A1 (en) | 2004-04-29 |
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