AU2003224546B2 - Heterocyclic compounds - Google Patents
Heterocyclic compounds Download PDFInfo
- Publication number
- AU2003224546B2 AU2003224546B2 AU2003224546A AU2003224546A AU2003224546B2 AU 2003224546 B2 AU2003224546 B2 AU 2003224546B2 AU 2003224546 A AU2003224546 A AU 2003224546A AU 2003224546 A AU2003224546 A AU 2003224546A AU 2003224546 B2 AU2003224546 B2 AU 2003224546B2
- Authority
- AU
- Australia
- Prior art keywords
- azabicyclo
- furo
- octane
- spiro
- prophylaxis
- 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.)
- Ceased
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 28
- 238000011321 prophylaxis Methods 0.000 claims description 26
- 125000003003 spiro group Chemical group 0.000 claims description 26
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 23
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 23
- 230000006735 deficit Effects 0.000 claims description 23
- 208000035475 disorder Diseases 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 229960002715 nicotine Drugs 0.000 claims description 11
- 208000028017 Psychotic disease Diseases 0.000 claims description 10
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 8
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 8
- 208000016620 Tourette disease Diseases 0.000 claims description 8
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 229910052722 tritium Inorganic materials 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 208000000044 Amnesia Diseases 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 206010026749 Mania Diseases 0.000 claims description 7
- 208000026139 Memory disease Diseases 0.000 claims description 7
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
- 230000003935 attention Effects 0.000 claims description 7
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- 208000028683 bipolar I disease Diseases 0.000 claims description 7
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- 210000000225 synapse Anatomy 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 6
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- 206010057852 Nicotine dependence Diseases 0.000 claims description 5
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 4
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 4
- 230000008484 agonism Effects 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- JNEIQTNYQGYWIF-INIZCTEOSA-N (3r)-5'-(1,3-thiazol-5-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C1=CN=CS1 JNEIQTNYQGYWIF-INIZCTEOSA-N 0.000 claims 1
- IAADVLIGDRQHCI-KRWDZBQOSA-N (3r)-5'-(2-methyl-1,3-thiazol-5-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(C)=NC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 IAADVLIGDRQHCI-KRWDZBQOSA-N 0.000 claims 1
- 241001446467 Mama Species 0.000 claims 1
- 101000585797 Rice gall dwarf virus Movement protein Proteins 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
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- 239000002904 solvent Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- -1 heterocyclic amines Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
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- 239000003446 ligand Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- YGFFDFKDCIJMIG-ZDUSSCGKSA-N (3r)-5'-bromospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2[C@@]11OC2=NC=C(Br)C=C2C1 YGFFDFKDCIJMIG-ZDUSSCGKSA-N 0.000 description 2
- WLQGXFSBIGJXDA-UHFFFAOYSA-N (4-bromo-1,3-thiazol-2-yl)-trimethylsilane Chemical compound C[Si](C)(C)C1=NC(Br)=CS1 WLQGXFSBIGJXDA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- 239000002775 capsule Substances 0.000 description 1
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- MUCZHBLJLSDCSD-UHFFFAOYSA-N diisopropyl fluorophosphate Chemical compound CC(C)OP(F)(=O)OC(C)C MUCZHBLJLSDCSD-UHFFFAOYSA-N 0.000 description 1
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- 239000002552 dosage form Substances 0.000 description 1
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- ZSWXYQDKHXCYPG-UHFFFAOYSA-N triethyl(1,3-thiazol-2-yl)stannane Chemical compound CC[Sn](CC)(CC)C1=NC=CS1 ZSWXYQDKHXCYPG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C07D491/22—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 four or more hetero rings
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Neurology (AREA)
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- Addiction (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
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|---|---|---|---|
| SE0201185-6 | 2002-04-18 | ||
| SE0201185A SE0201185D0 (sv) | 2002-04-18 | 2002-04-18 | Heterocyclic compounds |
| SE0203606-9 | 2002-12-04 | ||
| SE0203606A SE0203606D0 (sv) | 2002-12-04 | 2002-12-04 | Heterocyclic compounds |
| PCT/SE2003/000615 WO2003087104A1 (en) | 2002-04-18 | 2003-04-15 | Heterocyclic compounds |
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| AU2003224546A1 AU2003224546A1 (en) | 2003-10-27 |
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| JP (1) | JP4523775B2 (enExample) |
| KR (1) | KR20040099446A (enExample) |
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| AT (1) | ATE433981T1 (enExample) |
| AU (1) | AU2003224546B2 (enExample) |
| BR (1) | BR0309345A (enExample) |
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| ES (1) | ES2326638T3 (enExample) |
| HK (1) | HK1080470B (enExample) |
| IL (1) | IL164511A0 (enExample) |
| MX (1) | MXPA04010190A (enExample) |
| NO (1) | NO20044995L (enExample) |
| NZ (1) | NZ561993A (enExample) |
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| AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| KR100614900B1 (ko) | 2001-10-02 | 2006-08-25 | 파마시아 앤드 업존 캄파니 엘엘씨 | 질병의 치료를 위한 아자비시클릭-치환된 융합-헤테로아릴화합물 |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
| ES2649737T5 (es) | 2003-08-01 | 2021-07-07 | Mitsubishi Tanabe Pharma Corp | Compuestos novedosos que tienen actividad inhibidora frente a transportador de glucosa dependiente de sodio |
| CN1856497A (zh) * | 2003-09-25 | 2006-11-01 | 阿斯利康(瑞典)有限公司 | 配体 |
| KR20060094962A (ko) * | 2003-10-21 | 2006-08-30 | 아스트라제네카 아베 | 스피로푸로피리딘 아릴 유도체 |
| US7045530B2 (en) | 2003-12-22 | 2006-05-16 | Abbott Laboratories | Spirocyclic quinuclidinic ether derivatives |
| TW200813067A (en) | 2006-05-17 | 2008-03-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| UY30730A1 (es) | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| CA2699285C (en) | 2007-09-10 | 2016-12-13 | Ahmed F. Abdel-Magid | Process for the preparation of compounds useful as inhibitors of sodium-dependent glucose transporter (sglt) |
| CL2008003653A1 (es) | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| ES2325049B2 (es) * | 2008-02-21 | 2010-03-16 | Universidade De Santiago De Compostela | Deteccion y cuantificacion de iminas ciclicas basada en la union competitiva a receptores nicotinicos de acetilcolina. |
| RS52703B (sr) | 2008-06-20 | 2013-08-30 | Astrazeneca Ab | Derivat dibenzotiazepina i njegova upotreba |
| US9056850B2 (en) | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| IN2012DN03299A (enExample) | 2009-10-14 | 2015-10-23 | Janssen Pharmaceutica Nv | |
| SG185525A1 (en) | 2010-05-11 | 2012-12-28 | Janssen Pharmaceutica Nv | Pharmaceutical formulations comprising 1 - (beta-d-glucopyranosyl) - 2 -thienylmethylbenzene derivatives as inhibitors of sglt |
| PT3029039T (pt) | 2010-05-17 | 2017-11-28 | Forum Pharmaceuticals Inc | Formulações farmacêuticas que compreendem formas cristalinas de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida mono-hidratado |
| AU2012241897C1 (en) | 2011-04-13 | 2017-05-11 | Janssen Pharmaceutica Nv | Process for the preparation of compounds useful as inhibitors of SGLT2 |
| US9035044B2 (en) | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| EA029430B1 (ru) | 2013-06-21 | 2018-03-30 | Такеда Фармасьютикл Компани Лимитед | Производные 1-сульфонилпиперидина в качестве модуляторов рецепторов прокинетицина |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| US20170071970A1 (en) | 2015-09-15 | 2017-03-16 | Janssen Pharmaceutica Nv | Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003859A1 (en) * | 1997-07-18 | 1999-01-28 | Astra Aktiebolag | Novel spiroazabicyclic heterocyclic compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9900100D0 (sv) * | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| FR2788982B1 (fr) | 1999-02-02 | 2002-08-02 | Synthelabo | Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique |
| US6569865B2 (en) | 2001-06-01 | 2003-05-27 | Astrazeneca Ab | Spiro 1-azabicyclo[2.2.2]octane-3,2′(3′h)-furo[2,3-b]pyridine |
| CN1294136C (zh) | 2001-06-01 | 2007-01-10 | 阿斯特拉曾尼卡有限公司 | 用于治疗的烟碱乙酰胆碱受体新型配体 |
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2003
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- 2003-04-15 BR BR0309345-0A patent/BR0309345A/pt not_active IP Right Cessation
- 2003-04-15 CA CA002482313A patent/CA2482313A1/en not_active Abandoned
- 2003-04-15 DE DE60328010T patent/DE60328010D1/de not_active Expired - Lifetime
- 2003-04-15 JP JP2003584060A patent/JP4523775B2/ja not_active Expired - Fee Related
- 2003-04-15 EP EP03721209A patent/EP1499616B1/en not_active Expired - Lifetime
- 2003-04-15 US US10/511,525 patent/US7417050B2/en not_active Expired - Fee Related
- 2003-04-15 AT AT03721209T patent/ATE433981T1/de not_active IP Right Cessation
- 2003-04-15 ES ES03721209T patent/ES2326638T3/es not_active Expired - Lifetime
- 2003-04-15 NZ NZ561993A patent/NZ561993A/en unknown
- 2003-04-15 CN CNB038139014A patent/CN1325501C/zh not_active Expired - Fee Related
- 2003-04-15 WO PCT/SE2003/000615 patent/WO2003087104A1/en not_active Ceased
- 2003-04-15 AU AU2003224546A patent/AU2003224546B2/en not_active Ceased
- 2003-04-15 KR KR10-2004-7016545A patent/KR20040099446A/ko not_active Ceased
- 2003-04-15 HK HK06100288.5A patent/HK1080470B/zh not_active IP Right Cessation
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2004
- 2004-10-11 IL IL16451104A patent/IL164511A0/xx unknown
- 2004-11-17 NO NO20044995A patent/NO20044995L/no not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003859A1 (en) * | 1997-07-18 | 1999-01-28 | Astra Aktiebolag | Novel spiroazabicyclic heterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1499616A1 (en) | 2005-01-26 |
| HK1080470A1 (zh) | 2006-04-28 |
| IL164511A0 (en) | 2005-12-18 |
| US7417050B2 (en) | 2008-08-26 |
| KR20040099446A (ko) | 2004-11-26 |
| NZ561993A (en) | 2008-09-26 |
| JP2005534624A (ja) | 2005-11-17 |
| WO2003087104A1 (en) | 2003-10-23 |
| CN1325501C (zh) | 2007-07-11 |
| ES2326638T3 (es) | 2009-10-16 |
| CN1662542A (zh) | 2005-08-31 |
| CA2482313A1 (en) | 2003-10-23 |
| JP4523775B2 (ja) | 2010-08-11 |
| EP1499616B1 (en) | 2009-06-17 |
| NO20044995L (no) | 2005-01-18 |
| BR0309345A (pt) | 2005-02-15 |
| HK1080470B (zh) | 2008-03-07 |
| MXPA04010190A (es) | 2005-02-03 |
| DE60328010D1 (de) | 2009-07-30 |
| ATE433981T1 (de) | 2009-07-15 |
| AU2003224546A1 (en) | 2003-10-27 |
| US20050131003A1 (en) | 2005-06-16 |
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