UA79283C2 - Pyrrolidinium derivatives, process for the preparation thereof (variants), intermediate (variants), pharmaceutical composition, combined product - Google Patents
Pyrrolidinium derivatives, process for the preparation thereof (variants), intermediate (variants), pharmaceutical composition, combined product Download PDFInfo
- Publication number
- UA79283C2 UA79283C2 UA20041109322A UA20041109322A UA79283C2 UA 79283 C2 UA79283 C2 UA 79283C2 UA 20041109322 A UA20041109322 A UA 20041109322A UA 20041109322 A UA20041109322 A UA 20041109322A UA 79283 C2 UA79283 C2 UA 79283C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methyl
- hydroxy
- propyl
- dithien
- diastereomer
- Prior art date
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims abstract description 202
- 238000000034 method Methods 0.000 title claims abstract description 114
- 238000002360 preparation method Methods 0.000 title claims abstract description 54
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
- 239000005557 antagonist Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 234
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 129
- -1 5,6,7,8-tetrahydronaphthalenyl Chemical group 0.000 claims description 123
- 239000000203 mixture Substances 0.000 claims description 116
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 88
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 71
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 31
- FVEJUHUCFCAYRP-UHFFFAOYSA-N 2-hydroxy-2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(O)(C(=O)O)C1=CC=CS1 FVEJUHUCFCAYRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 14
- CKNYWTABPYGPEX-UHFFFAOYSA-N pyrrolidin-1-ium;2,2,2-trifluoroacetate Chemical compound C1CC[NH2+]C1.[O-]C(=O)C(F)(F)F CKNYWTABPYGPEX-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 208000023504 respiratory system disease Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 10
- 229940100198 alkylating agent Drugs 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 208000014001 urinary system disease Diseases 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 208000012931 Urologic disease Diseases 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- XAXGLDHLTLQVOD-UHFFFAOYSA-N pyrrolidin-1-ium;formate Chemical compound [O-]C=O.C1CC[NH2+]C1 XAXGLDHLTLQVOD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 230000000241 respiratory effect Effects 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 208000010643 digestive system disease Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 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 description 4
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000004820 halides Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 239000000043 antiallergic agent Substances 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002617 leukotrienes Chemical class 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000007519 polyprotic acids Polymers 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims 5
- 230000003993 interaction Effects 0.000 claims 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 1
- OCGXMFPEZREITF-UHFFFAOYSA-M [1-ethyl-1-(3-phenylsulfanylpropyl)pyrrolidin-1-ium-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC(OC(=O)C(O)(C2CCCCC2)C=2OC=CC=2)C[N+]1(CC)CCCSC1=CC=CC=C1 OCGXMFPEZREITF-UHFFFAOYSA-M 0.000 claims 1
- XKLNKVSZPXNGCT-UHFFFAOYSA-M [1-methyl-1-(3-pyrrol-1-ylpropyl)pyrrolidin-1-ium-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC(OC(=O)C(O)(C=2SC=CC=2)C=2SC=CC=2)C[N+]1(C)CCCN1C=CC=C1 XKLNKVSZPXNGCT-UHFFFAOYSA-M 0.000 claims 1
- XTVSCNWFFGBOTF-UHFFFAOYSA-M [1-methyl-1-(4-oxo-4-thiophen-2-ylbutyl)pyrrolidin-1-ium-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC(OC(=O)C(O)(C=2SC=CC=2)C=2SC=CC=2)C[N+]1(C)CCCC(=O)C1=CC=CS1 XTVSCNWFFGBOTF-UHFFFAOYSA-M 0.000 claims 1
- 210000005056 cell body Anatomy 0.000 claims 1
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 94
- 238000005481 NMR spectroscopy Methods 0.000 description 83
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
-
- 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
-
- 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
-
- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200200889A ES2206021B1 (es) | 2002-04-16 | 2002-04-16 | Nuevos derivados de pirrolidinio. |
| PCT/EP2003/003786 WO2003087094A2 (fr) | 2002-04-16 | 2003-04-11 | Nouveaux derives du pyrrolidinium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79283C2 true UA79283C2 (en) | 2007-06-11 |
Family
ID=29225796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041109322A UA79283C2 (en) | 2002-04-16 | 2003-11-04 | Pyrrolidinium derivatives, process for the preparation thereof (variants), intermediate (variants), pharmaceutical composition, combined product |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7192978B2 (fr) |
| EP (1) | EP1497284A2 (fr) |
| CN (1) | CN100548978C (fr) |
| AR (1) | AR039412A1 (fr) |
| AU (1) | AU2003233967B2 (fr) |
| BR (1) | BR0309167A (fr) |
| CA (1) | CA2482536A1 (fr) |
| CO (1) | CO5611106A2 (fr) |
| ES (1) | ES2206021B1 (fr) |
| IL (1) | IL164522A0 (fr) |
| MX (1) | MXPA04010076A (fr) |
| MY (1) | MY137535A (fr) |
| NO (1) | NO20044826L (fr) |
| NZ (1) | NZ535884A (fr) |
| PE (1) | PE20040409A1 (fr) |
| RU (1) | RU2320657C2 (fr) |
| TW (1) | TW200403237A (fr) |
| UA (1) | UA79283C2 (fr) |
| UY (1) | UY27760A1 (fr) |
| WO (1) | WO2003087094A2 (fr) |
| ZA (1) | ZA200408335B (fr) |
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|---|---|---|---|---|
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| PE20050231A1 (es) * | 2003-06-24 | 2005-05-20 | Novartis Ag | Derivados de piperidinium y pirrolidinium como antagonistas del receptor muscarinico m3 |
| US20050026887A1 (en) * | 2003-07-29 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a steroid |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| JP2007530451A (ja) * | 2004-03-11 | 2007-11-01 | グラクソ グループ リミテッド | 新規ｍ３ムスカリン性アセチルコリン受容体アンタゴニスト |
| TWI363759B (en) | 2004-04-27 | 2012-05-11 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| PL1891974T3 (pl) * | 2004-05-31 | 2010-12-31 | Almirall Sa | Kombinacje zawierające środki przeciwmuskarynowe i inhibitory PDE4 |
| ES2257152B1 (es) * | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| GB0428418D0 (en) * | 2004-12-24 | 2005-02-02 | Novartis Ag | Organic compounds |
| GB0428416D0 (en) * | 2004-12-24 | 2005-02-02 | Novartis Ag | Organic compounds |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| TW200722418A (en) * | 2005-04-20 | 2007-06-16 | Astrazeneca Ab | Novel compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| US7994211B2 (en) * | 2005-08-08 | 2011-08-09 | Argenta Discovery Limited | Bicyclo[2.2.1]hept-7-ylamine derivatives and their uses |
| US7910708B2 (en) | 2005-10-21 | 2011-03-22 | Novartis Ag | Anti-IL13 human antibodies |
| EP1971572A1 (fr) * | 2005-12-16 | 2008-09-24 | Argenta Discovery Limited | Derives d'amines cycliques et utilisation de ceux-ci |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| KR20080110925A (ko) | 2006-04-21 | 2008-12-19 | 노파르티스 아게 | 아데노신 ａ２ａ 수용체 효능제로서 사용하기 위한 퓨린 유도체 |
| ES2298049B1 (es) | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| DE602007013441D1 (de) | 2006-09-29 | 2011-05-05 | Novartis Ag | Pyrazolopyrimidine als pi3k-lipidkinasehemmer |
| TW200825084A (en) | 2006-11-14 | 2008-06-16 | Astrazeneca Ab | New compounds 521 |
| WO2008075006A1 (fr) * | 2006-12-19 | 2008-06-26 | Astrazeneca Ab | Composés de piperldinum pour le traitement de maladies pulmonaires obstructives |
| DE602007011670D1 (de) | 2007-01-10 | 2011-02-10 | Irm Llc | Verbindungen und zusammensetzungen als kanal-aktivierende proteasehemmer |
| WO2008096094A1 (fr) * | 2007-02-06 | 2008-08-14 | Argenta Discovery Ltd. | Dérivés de bicyclor[2.2.1]hept-7-ylamine utile comme modulateur du récepteur m3 muscarinique |
| CA2675942C (fr) * | 2007-02-23 | 2016-04-12 | Theravance, Inc. | Composes de diphenylmethyle d'ammonium quartenaire utilises comme antagonistes de recepteur muscarinique |
| BRPI0811562A2 (pt) | 2007-05-07 | 2014-12-09 | Novartis Ag | Compostos orgânicos |
| WO2009035542A2 (fr) | 2007-09-07 | 2009-03-19 | Theravance, Inc. | Composés contenant de la guanidine utilisés en tant qu'antagonistes du récepteur muscarinique |
| CA2608561A1 (fr) * | 2007-10-29 | 2009-04-29 | Carl Paluszkiewicz | Support d'accessoires de deflecteur pour motocyclette |
| EP2231280B1 (fr) | 2007-12-10 | 2016-08-10 | Novartis AG | Pyrazine carboxamides semblable à l'Amiloride en tant que bloqueurs d'ENaC |
| EP2222637A1 (fr) | 2007-12-14 | 2010-09-01 | Theravance, Inc. | Composés contenant de l'amidine utiles comme antagonistes du récepteur muscarinique |
| PL2231642T3 (pl) | 2008-01-11 | 2014-04-30 | Novartis Ag | Pirymidyny jako inhibitory kinazy |
| EP2100598A1 (fr) * | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Composition à inhaler comprenant aclidinium pour le traitement de l'asthme et de maladies respiratoires obstructives chroniques |
| EP2100599A1 (fr) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Composition à inhaler comprenant aclidinium pour le traitement de l'asthme et de maladies respiratoires obstructives chroniques |
| US8268834B2 (en) | 2008-03-19 | 2012-09-18 | Novartis Ag | Pyrazine derivatives that inhibit phosphatidylinositol 3-kinase enzyme |
| EA017627B1 (ru) | 2008-05-13 | 2013-01-30 | Астразенека Аб | Хинуклидиновые производные в качестве антагонистов мускаринового м3 рецептора |
| US8236808B2 (en) | 2008-06-10 | 2012-08-07 | Novartis Ag | Pyrazine derivatives as ENAC blockers |
| PT2391366E (pt) | 2009-01-29 | 2013-02-05 | Novartis Ag | Benzimidazoles substituídos para o tratamento de astrocitomas |
| WO2010115937A1 (fr) * | 2009-04-09 | 2010-10-14 | Novartis Ag | Procédé de préparation de sels de pyrrolidinium |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| EP2464649A1 (fr) | 2009-08-12 | 2012-06-20 | Novartis AG | Composés hydrazone hétérocycliques et leurs utilisations pour traiter le cancer et l'inflammation |
| NZ598220A (en) | 2009-08-17 | 2014-02-28 | Intellikine Llc | Heterocyclic compounds and uses thereof |
| CA2771432A1 (fr) | 2009-08-20 | 2011-02-24 | Novartis Ag | Composes d'oximes heterocycliques |
| CA2777245A1 (fr) | 2009-10-22 | 2011-04-28 | Vertex Pharmaceuticals Incorporated | Compositions destinees au traitement de la mucoviscidose et d'autres maladies chroniques |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (fr) | 2010-09-09 | 2012-03-15 | Irm Llc | Composés et compositions comme inhibiteurs de trk |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| JP2014505088A (ja) | 2011-02-10 | 2014-02-27 | ノバルティス アーゲー | Ｃ−ＭＥＴチロシンキナーゼ阻害剤としての［１，２，４］トリアゾロ［４，３−ｂ］ピリダジン化合物 |
| JP5808826B2 (ja) | 2011-02-23 | 2015-11-10 | インテリカイン， エルエルシー | 複素環化合物およびその使用 |
| US9102671B2 (en) | 2011-02-25 | 2015-08-11 | Novartis Ag | Compounds and compositions as TRK inhibitors |
| EP2510928A1 (fr) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium pour l'amélioration du sommeil des patients avec des maldadies respiratoires |
| UY34305A (es) | 2011-09-01 | 2013-04-30 | Novartis Ag | Derivados de heterociclos bicíclicos para el tratamiento de la hipertensión arterial pulmonar |
| UY34329A (es) | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
| WO2013038381A1 (fr) | 2011-09-16 | 2013-03-21 | Novartis Ag | Dérivés d'amide pyridine/pyrazine |
| ES2558457T3 (es) | 2011-09-16 | 2016-02-04 | Novartis Ag | Compuestos heterocíclicos para el tratamiento de fibrosis quística |
| WO2013038378A1 (fr) | 2011-09-16 | 2013-03-21 | Novartis Ag | Dérivés pyridinamides |
| WO2013038373A1 (fr) | 2011-09-16 | 2013-03-21 | Novartis Ag | Dérivés pyrimidinamides |
| EP2755652B1 (fr) | 2011-09-16 | 2021-06-02 | Novartis AG | Hétérocyclyle carboxamides n-substitués |
| US9174994B2 (en) | 2011-11-23 | 2015-11-03 | Intellikine, Llc | Enhanced treatment regimens using mTor inhibitors |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| CN104245701A (zh) | 2012-04-03 | 2014-12-24 | 诺华有限公司 | 有酪氨酸激酶抑制剂的组合产品和其应用 |
| US9156833B2 (en) | 2012-07-16 | 2015-10-13 | Barry University, Inc. | Bitopic muscarinic agonists and antagonists and methods of synthesis and use thereof |
| CN103965178B (zh) * | 2013-02-06 | 2018-03-02 | 中国药科大学 | 作为m3毒蕈碱性受体拮抗剂的吡咯烷鎓衍生物及其在制药中的用途 |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| EP2968340A4 (fr) | 2013-03-15 | 2016-08-10 | Intellikine Llc | Combinaison d'inhibiteurs de kinase et ses utilisations |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
| BR112016023967A2 (pt) | 2014-04-24 | 2017-08-15 | Novartis Ag | derivados de pirazina como inibidores de fosfatidilinositol 3-cinase |
| JP6433509B2 (ja) | 2014-04-24 | 2018-12-05 | ノバルティス アーゲー | ホスファチジルイノシトール３−キナーゼ阻害薬としてのアミノピラジン誘導体 |
| WO2015162456A1 (fr) | 2014-04-24 | 2015-10-29 | Novartis Ag | Dérivés aminés de pyridine utilisables en tant qu'inhibiteurs de la phosphatidylinositol 3-kinase |
| WO2016011658A1 (fr) | 2014-07-25 | 2016-01-28 | Novartis Ag | Polythérapie |
| KR20170036037A (ko) | 2014-07-31 | 2017-03-31 | 노파르티스 아게 | 조합 요법 |
| CN105085355B (zh) * | 2015-06-25 | 2017-11-14 | 御盛隆堂药业有限责任公司 | 一种取代的吡咯烷羧酸酯类化合物及其制备方法和应用 |
| ES2805031T3 (es) | 2016-02-10 | 2021-02-10 | Sumitomo Chemical Co | Método de producción de 1-metilpirrolidin-3-ol |
| JP7161466B2 (ja) | 2016-08-02 | 2022-10-26 | ジャーニー メディカル コーポレーション | グリコピロニウム化合物を作製するための方法及び使用する方法 |
| US20200383960A1 (en) | 2019-06-10 | 2020-12-10 | Novartis Ag | Pyridine and Pyrazine derivative for the Treatment of CF, COPD, and Bronchiectasis |
| JP2022547427A (ja) | 2019-08-28 | 2022-11-14 | ノバルティス アーゲー | 置換１，３－フェニルヘテロアリール誘導体及び疾患の治療におけるその使用 |
| TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗ｔｓｌｐ抗體治療炎性或阻塞性氣道疾病之方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956062A (en) | 1959-02-26 | 1960-10-11 | Robins Co Inc A H | Esters of amino alcohols |
| US3301869A (en) * | 1960-05-16 | 1967-01-31 | Robins Co Inc A H | Methobromide and hydrochloride of 1-ethyl-3-pyrrolidyl benzilate |
| GB1219606A (en) * | 1968-07-15 | 1971-01-20 | Rech S Et D Applic Scient Soge | Quinuclidinol derivatives and preparation thereof |
| FR2155927A1 (en) * | 1971-10-15 | 1973-05-25 | Synthelabo | 1-phenylcyclo hexane carboxylic acid esters - with antispasmodic and anticholinergic activity |
| JPS5679688A (en) * | 1979-12-04 | 1981-06-30 | Ota Seiyaku Kk | 4-acyloxy-1- 1,3-dioxoran-2-ylmethyl piperidine derivative and its production |
| EP0863141B1 (fr) * | 1995-10-13 | 2001-09-12 | Banyu Pharmaceutical Co., Ltd. | Derives heteroaromatiques substitues |
| US6613795B2 (en) | 1996-11-11 | 2003-09-02 | Christian Noe | Enantiomerically pure basic arylcycloalkylhydroxycarboxylic esters, processes for their preparation and their use in medicaments |
| DK0937041T3 (da) * | 1996-11-11 | 2003-08-11 | Christian R Noe | Anvendelse af et farmaceutisk egnet salt af (3R,2'R)-3-[(cyclopentil-hydroxyphenylacetyl)oxyl]-1,1-dimethyl-pyrrolidinium til fremstilling af et lægemiddel |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| WO2002005590A1 (fr) * | 2000-06-30 | 2002-01-17 | Cochlear Limited | Implant cochleaire |
| EP1302458A4 (fr) | 2000-07-11 | 2005-10-19 | Banyu Pharma Co Ltd | Derives d'ester |
| US7174126B2 (en) * | 2002-05-03 | 2007-02-06 | Time Warner Interactive Video Group Inc. | Technique for effectively accessing programming listing information in an entertainment delivery system |
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2002
- 2002-04-16 ES ES200200889A patent/ES2206021B1/es not_active Expired - Fee Related
-
2003
- 2003-04-10 UY UY27760A patent/UY27760A1/es not_active Application Discontinuation
- 2003-04-11 BR BR0309167-8A patent/BR0309167A/pt not_active IP Right Cessation
- 2003-04-11 WO PCT/EP2003/003786 patent/WO2003087094A2/fr not_active Application Discontinuation
- 2003-04-11 US US10/510,680 patent/US7192978B2/en not_active Expired - Fee Related
- 2003-04-11 MX MXPA04010076A patent/MXPA04010076A/es active IP Right Grant
- 2003-04-11 AU AU2003233967A patent/AU2003233967B2/en not_active Ceased
- 2003-04-11 EP EP03727294A patent/EP1497284A2/fr not_active Withdrawn
- 2003-04-11 NZ NZ535884A patent/NZ535884A/en unknown
- 2003-04-11 RU RU2004133371/04A patent/RU2320657C2/ru not_active IP Right Cessation
- 2003-04-11 CA CA002482536A patent/CA2482536A1/fr not_active Abandoned
- 2003-04-11 CN CNB038138921A patent/CN100548978C/zh not_active Expired - Fee Related
- 2003-04-14 AR ARP030101294A patent/AR039412A1/es unknown
- 2003-04-15 PE PE2003000381A patent/PE20040409A1/es not_active Application Discontinuation
- 2003-04-15 MY MYPI20031408A patent/MY137535A/en unknown
- 2003-04-16 TW TW092108810A patent/TW200403237A/zh unknown
- 2003-11-04 UA UA20041109322A patent/UA79283C2/uk unknown
-
2004
- 2004-10-12 IL IL16452204A patent/IL164522A0/xx unknown
- 2004-10-14 ZA ZA200408335A patent/ZA200408335B/xx unknown
- 2004-10-15 CO CO04104136A patent/CO5611106A2/es not_active Application Discontinuation
- 2004-11-05 NO NO20044826A patent/NO20044826L/no not_active Application Discontinuation
-
2007
- 2007-01-03 US US11/648,581 patent/US20070129420A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TW200403237A (en) | 2004-03-01 |
| AU2003233967A1 (en) | 2003-10-27 |
| MY137535A (en) | 2009-02-27 |
| NO20044826L (no) | 2005-01-14 |
| NZ535884A (en) | 2007-11-30 |
| CN100548978C (zh) | 2009-10-14 |
| EP1497284A2 (fr) | 2005-01-19 |
| IL164522A0 (en) | 2005-12-18 |
| CA2482536A1 (fr) | 2003-10-23 |
| AR039412A1 (es) | 2005-02-16 |
| UY27760A1 (es) | 2003-11-28 |
| PE20040409A1 (es) | 2004-07-14 |
| RU2004133371A (ru) | 2005-08-10 |
| ZA200408335B (en) | 2005-11-02 |
| US20050282875A1 (en) | 2005-12-22 |
| BR0309167A (pt) | 2005-01-25 |
| RU2320657C2 (ru) | 2008-03-27 |
| CN1662527A (zh) | 2005-08-31 |
| WO2003087094A3 (fr) | 2004-03-18 |
| CO5611106A2 (es) | 2006-02-28 |
| ES2206021A1 (es) | 2004-05-01 |
| US7192978B2 (en) | 2007-03-20 |
| WO2003087094A2 (fr) | 2003-10-23 |
| US20070129420A1 (en) | 2007-06-07 |
| MXPA04010076A (es) | 2004-12-13 |
| ES2206021B1 (es) | 2005-08-01 |
| AU2003233967B2 (en) | 2009-08-06 |
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