RU2356888C2 - Новые азетидиновые соединения - Google Patents
Новые азетидиновые соединения Download PDFInfo
- Publication number
- RU2356888C2 RU2356888C2 RU2005136535/04A RU2005136535A RU2356888C2 RU 2356888 C2 RU2356888 C2 RU 2356888C2 RU 2005136535/04 A RU2005136535/04 A RU 2005136535/04A RU 2005136535 A RU2005136535 A RU 2005136535A RU 2356888 C2 RU2356888 C2 RU 2356888C2
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- fluorophenyl
- butyl
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- 150000001539 azetidines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 150000003839 salts Chemical class 0.000 claims abstract 9
- -1 cyano, 1,3-dioxolan-2-yl Chemical group 0.000 claims abstract 7
- 239000003814 drug Substances 0.000 claims abstract 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 230000003042 antagnostic effect Effects 0.000 claims abstract 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims abstract 3
- 230000002757 inflammatory effect Effects 0.000 claims abstract 3
- 230000000241 respiratory effect Effects 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract 2
- 230000000771 oncological effect Effects 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 230000001354 painful effect Effects 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 4
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 206010046543 Urinary incontinence Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 230000003993 interaction Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 206010047700 Vomiting Diseases 0.000 claims 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 230000002496 gastric effect Effects 0.000 claims 2
- 230000030136 gastric emptying Effects 0.000 claims 2
- 230000030135 gastric motility Effects 0.000 claims 2
- 230000035873 hypermotility Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000008673 vomiting Effects 0.000 claims 2
- DXACPHMYDLQPGI-MRXNPFEDSA-N (2s)-2-(4-fluorophenyl)-n-methyl-4-(3-morpholin-4-ylazetidin-1-yl)butan-1-amine Chemical compound C([C@H](CNC)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCOCC1 DXACPHMYDLQPGI-MRXNPFEDSA-N 0.000 claims 1
- PKBBOUFAWOJQCG-UHFFFAOYSA-N 1-[1-[3-(4-fluorophenyl)-4-(methylamino)butyl]azetidin-3-yl]piperidin-4-ol Chemical compound C=1C=C(F)C=CC=1C(CNC)CCN(C1)CC1N1CCC(O)CC1 PKBBOUFAWOJQCG-UHFFFAOYSA-N 0.000 claims 1
- NZBIBDUDNNLOOY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-4-(3-thiomorpholin-4-ylazetidin-1-yl)butan-1-amine Chemical compound C=1C=C(F)C=CC=1C(CNC)CCN(C1)CC1N1CCSCC1 NZBIBDUDNNLOOY-UHFFFAOYSA-N 0.000 claims 1
- ZKOSIPOWFKYMQG-LJQANCHMSA-N 3,5-dibromo-n-[(2s)-2-(4-fluorophenyl)-4-(3-morpholin-4-ylazetidin-1-yl)butyl]-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(Br)C=C(Br)C=1)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCOCC1 ZKOSIPOWFKYMQG-LJQANCHMSA-N 0.000 claims 1
- AYHRZURSFYCWMW-LJQANCHMSA-N 3,5-dibromo-n-[(2s)-2-(4-fluorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl]-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(Br)C=C(Br)C=1)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCC(O)CC1 AYHRZURSFYCWMW-LJQANCHMSA-N 0.000 claims 1
- DDRUQVHZZJJNQS-CYBMUJFWSA-N 3,5-dibromo-n-[(2s)-2-(4-fluorophenyl)-4-oxobutyl]-n-methylbenzamide Chemical compound C1([C@H](CC=O)CN(C)C(=O)C=2C=C(Br)C=C(Br)C=2)=CC=C(F)C=C1 DDRUQVHZZJJNQS-CYBMUJFWSA-N 0.000 claims 1
- PFUDFVJHHRDNCG-CYBMUJFWSA-N 3,5-dichloro-n-[(2s)-2-(4-fluorophenyl)-4-oxobutyl]-n-methylbenzamide Chemical compound C1([C@H](CC=O)CN(C)C(=O)C=2C=C(Cl)C=C(Cl)C=2)=CC=C(F)C=C1 PFUDFVJHHRDNCG-CYBMUJFWSA-N 0.000 claims 1
- DVYSFOLDYKOTBZ-LJQANCHMSA-N 3-fluoro-n-[(2s)-2-(4-fluorophenyl)-4-(3-morpholin-4-ylazetidin-1-yl)butyl]-n-methyl-5-(trifluoromethyl)benzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(C=C(F)C=1)C(F)(F)F)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCOCC1 DVYSFOLDYKOTBZ-LJQANCHMSA-N 0.000 claims 1
- AZJZOMOXXVGTBU-UHFFFAOYSA-N 4-[3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)azetidin-1-yl]-2-(4-fluorophenyl)-n-methylbutan-1-amine Chemical compound C=1C=C(F)C=CC=1C(CNC)CCN(C1)CC1N(CC1)CCC21OCCO2 AZJZOMOXXVGTBU-UHFFFAOYSA-N 0.000 claims 1
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- 125000003172 aldehyde group Chemical group 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 claims 1
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- 239000000969 carrier Substances 0.000 claims 1
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- 239000003085 diluting agent Substances 0.000 claims 1
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- 230000001747 exhibiting effect Effects 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- IIBVUAKNSSXKMY-LJQANCHMSA-N n-[(2s)-2-(4-fluorophenyl)-4-[3-(4-fluoropiperidin-1-yl)azetidin-1-yl]butyl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCC(F)CC1 IIBVUAKNSSXKMY-LJQANCHMSA-N 0.000 claims 1
- XRKUJNRSSZKHRU-LJQANCHMSA-N n-[(2s)-2-(4-fluorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCC(O)CC1 XRKUJNRSSZKHRU-LJQANCHMSA-N 0.000 claims 1
- RLGBPDWDLDPHML-UHFFFAOYSA-N n-[2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)CC(C=1C=CC(F)=CC=1)CCN(C1)CC1N1CCSCC1 RLGBPDWDLDPHML-UHFFFAOYSA-N 0.000 claims 1
- NLDUHAPPNLENCT-UHFFFAOYSA-N n-[2-(4-fluorophenyl)-4-[3-(4-oxopiperidin-1-yl)azetidin-1-yl]butyl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)CC(C=1C=CC(F)=CC=1)CCN(C1)CC1N1CCC(=O)CC1 NLDUHAPPNLENCT-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 230000002485 urinary effect Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Pain & Pain Management (AREA)
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- Addiction (AREA)
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Applications Claiming Priority (4)
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| SE0301744-9 | 2003-06-13 | ||
| SE0301744A SE0301744D0 (sv) | 2003-06-13 | 2003-06-13 | New compounds |
| SE0303493-1 | 2003-12-19 | ||
| SE0303493A SE0303493D0 (sv) | 2003-12-19 | 2003-12-19 | New compounds |
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| RU2005136535A RU2005136535A (ru) | 2006-07-27 |
| RU2356888C2 true RU2356888C2 (ru) | 2009-05-27 |
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| RU (1) | RU2356888C2 (enExample) |
| TW (1) | TW200508221A (enExample) |
| WO (1) | WO2004110344A2 (enExample) |
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| SE0403005D0 (sv) * | 2004-12-09 | 2004-12-09 | Astrazeneca Ab | New use |
| CN101208327A (zh) * | 2005-06-23 | 2008-06-25 | 阿斯利康(瑞典)有限公司 | 作为神经激肽受体拮抗剂用于治疗胃肠疾病的新氮杂环丁烷衍生物 |
| AU2006259891A1 (en) * | 2005-06-23 | 2006-12-28 | Albireo Ab | New azetidine derivatives as neurokinin receptor antagonists for the treatment of gastrointestinal diseases |
| AR056087A1 (es) * | 2005-09-29 | 2007-09-19 | Astrazeneca Ab | Derivados de azetidina como antagonistas de receptores de neuroquina nk |
| AR057828A1 (es) * | 2005-09-29 | 2007-12-19 | Astrazeneca Ab | Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica |
| WO2007043938A1 (en) * | 2005-10-07 | 2007-04-19 | Astrazeneca Ab | NOVEL CRYSTALLINE FORM OF 3,5-DIBROMO-N- [ (2S) -2- (-4- FLUOROPHENYL) -4- (3-MORPHOLIN-4-YLAZTIDIN-l-YL) BUTYL] -N METHYLBENZAMIDE, MODIFICATION B |
| WO2007043939A1 (en) * | 2005-10-07 | 2007-04-19 | Astrazeneca Ab | Novel crystalline form of 3,5-dibromo-n- [(2s)-2-(-4-fluorophenyl)-4-(3-morpholin-4-ylazetidin-1-yl)butyl] -n-methylbenzamide, modification a |
| US8106208B2 (en) * | 2006-05-18 | 2012-01-31 | Albireo Ab | Benzamide compounds that act as NK receptor antagonists |
| WO2007136325A1 (en) * | 2006-05-18 | 2007-11-29 | Astrazeneca Ab | 1- [ (4- [benzoyl (methyl) amino] -3- (phenyl) butyl] azetidine derivatives for the treatment of gastrointestinal disorders 2 |
| WO2007136326A2 (en) * | 2006-05-18 | 2007-11-29 | Astrazeneca Ab | ) t e text as een esta s e y t s ut o ty to rea as o ows: 1- [ (4- [benzoyl (methyl) amino] -3- (phenyl) butyl] azetidine derivatives for the treatment of gastrointestinal disorders 3 |
| CL2007002097A1 (es) * | 2006-07-20 | 2008-01-18 | Smithkline Beecham Corp | Compuestos derivados de pirrolidina o morfolina antagonistas de urotensina ii; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar insuficiencia cardiaca congestiva, insuficiencia cardiaca isquemica, angina, isquemia del miocardio, vejiga hiperactiva, asma y/o copd, entre otras. |
| AU2007285371A1 (en) * | 2006-08-15 | 2008-02-21 | Actelion Pharmaceuticals Ltd. | Azetidine compounds as orexin receptor antagonists |
| WO2008076042A1 (en) * | 2006-12-19 | 2008-06-26 | Astrazeneca Ab | Azetidinpiperazine derivatives that are neurokinin (nk) receptor antagonists and their use. |
| WO2008076041A1 (en) * | 2006-12-19 | 2008-06-26 | Albireo Ab | Azetidinazabicyclo [3.2.1] octan derivatives that are neurokinin (nk) receptor antagonists and their use. |
| PL2125711T3 (pl) * | 2007-03-08 | 2014-05-30 | Albireo Ab | Pochodne kwasy 3-fenylopropionowego oraz ich zastosowanie w leczeniu nieswoistego zapalenia jelit |
| WO2008118092A1 (en) * | 2007-03-28 | 2008-10-02 | Albireo Ab | Maleate salt of 3-bromo-n-{ (2s) -2- (4-f luorophenyl) -4- [3- (4-acetylpiperazin-1-yl) azetidin-1-yl] butyl} -methyl-5- (trifluoromethyl)benzamide for the treatment of gastrointestinal disorders |
| WO2008118091A1 (en) * | 2007-03-28 | 2008-10-02 | Albireo Ab | A fumarate salt of 3-bromo-n-{ (2s) -2- (4 -fluorophenyl) -4- [3- (4-acetylpiperazin-l-yl) azetidin-1-yl] butyl} -n-methyl-5- (trifluoromethyl)benzamide for the treatment of gastrointestinal disorders |
| CN102105483A (zh) * | 2008-07-22 | 2011-06-22 | 纽约哥伦比亚大学理事会 | 甲基化分析的通用方法 |
| US10337049B2 (en) | 2013-06-17 | 2019-07-02 | The Trustees Of Columbia University In The City Of New York | Universal methylation profiling methods |
| CN113603670B (zh) * | 2021-07-23 | 2022-07-29 | 阜阳欣奕华制药科技有限公司 | 一种制备1-(7-溴苯并并[d][1,3]二氧杂环戊烯-4-基)乙-1-酮的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0791592B1 (en) * | 1996-01-27 | 2003-05-21 | Pfizer Limited | Azetidines |
Family Cites Families (22)
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| FI97540C (fi) * | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
| GB9310066D0 (en) | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Alkyl substituted heterocycles |
| GB9310713D0 (en) | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Aryl substituted heterocycles |
| GB9317104D0 (en) | 1993-08-17 | 1993-09-29 | Zeneca Ltd | Therapeutic heterocycles |
| GB9322643D0 (en) | 1993-11-03 | 1993-12-22 | Zeneca Ltd | Lactam derivatives |
| GB9325284D0 (en) | 1993-12-10 | 1994-02-16 | Rhone Poulenc Agriculture | Herbicidal compositions |
| TW432061B (en) | 1994-08-09 | 2001-05-01 | Pfizer Res & Dev | Lactams |
| US5607936A (en) * | 1994-09-30 | 1997-03-04 | Merck & Co., Inc. | Substituted aryl piperazines as neurokinin antagonists |
| GB9502644D0 (en) | 1995-02-10 | 1995-03-29 | Zeneca Ltd | Heterocyclic derivatives |
| GB9600235D0 (en) | 1996-01-05 | 1996-03-06 | Pfizer Ltd | Therapeutic agents |
| GB9601202D0 (en) * | 1996-01-22 | 1996-03-20 | Pfizer Ltd | Piperidones |
| GB9601680D0 (en) | 1996-01-27 | 1996-03-27 | Pfizer Ltd | Therapeutic agents |
| GB9714129D0 (en) | 1997-07-04 | 1997-09-10 | Pfizer Ltd | Azetidines |
| US6013652A (en) * | 1997-12-04 | 2000-01-11 | Merck & Co., Inc. | Spiro-substituted azacycles as neurokinin antagonists |
| GB9812037D0 (en) | 1998-06-04 | 1998-07-29 | Pfizer Ltd | Piperidones |
| KR20010083100A (ko) | 1998-07-10 | 2001-08-31 | 다비드 에 질레스 | 뉴로키닌-수용체 길항제로서 n-치환된 나프탈렌카르복스아미드 |
| GB9922519D0 (en) | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
| GB9922521D0 (en) | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
| GB9924141D0 (en) | 1998-10-30 | 1999-12-15 | Zeneca Ltd | Treatment of gastric asthma |
| GB9826941D0 (en) * | 1998-12-09 | 1999-02-03 | Zeneca Pharmaceuticals | Compounds |
| SE0004827D0 (sv) | 2000-12-22 | 2000-12-22 | Astrazeneca Ab | Therapeutic compounds |
| SE0103795D0 (sv) | 2001-11-02 | 2001-11-02 | Astrazeneca Ab | Compounds and method for the treatment of överactive bladder |
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- 2004-06-09 PL PL04736475T patent/PL1636221T3/pl unknown
- 2004-06-09 RU RU2005136535/04A patent/RU2356888C2/ru not_active IP Right Cessation
- 2004-06-09 US US10/560,319 patent/US7402581B2/en not_active Expired - Fee Related
- 2004-06-09 KR KR1020057023907A patent/KR20060021373A/ko not_active Withdrawn
- 2004-06-09 EP EP04736475A patent/EP1636221B1/en not_active Expired - Lifetime
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- 2005-12-07 CO CO05124364A patent/CO5640122A2/es not_active Application Discontinuation
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- 2006-01-11 IS IS8228A patent/IS8228A/is unknown
- 2006-01-13 NO NO20060206A patent/NO332109B1/no not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0791592B1 (en) * | 1996-01-27 | 2003-05-21 | Pfizer Limited | Azetidines |
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| HK1088004A1 (en) | 2006-10-27 |
| NO20060206L (no) | 2006-03-13 |
| KR20060021373A (ko) | 2006-03-07 |
| CA2529126C (en) | 2011-11-08 |
| IS8228A (is) | 2006-01-11 |
| ES2330522T3 (es) | 2009-12-11 |
| MXPA05013276A (es) | 2006-03-09 |
| ATE439358T1 (de) | 2009-08-15 |
| AU2004246983B2 (en) | 2008-06-12 |
| WO2004110344A2 (en) | 2004-12-23 |
| RU2005136535A (ru) | 2006-07-27 |
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| IL171894A (en) | 2012-05-31 |
| NO332109B1 (no) | 2012-06-25 |
| PL1636221T3 (pl) | 2010-01-29 |
| WO2004110344A3 (en) | 2005-02-17 |
| MY146599A (en) | 2012-08-30 |
| DE602004022546D1 (de) | 2009-09-24 |
| CA2529126A1 (en) | 2004-12-23 |
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| AR044662A1 (es) | 2005-09-21 |
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| JP4982886B2 (ja) | 2012-07-25 |
| DK1636221T3 (da) | 2009-10-12 |
| EP1636221A2 (en) | 2006-03-22 |
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