ZA200204553B - Urea compounds having muscarinic receptor antagonist activity. - Google Patents
Urea compounds having muscarinic receptor antagonist activity. Download PDFInfo
- Publication number
- ZA200204553B ZA200204553B ZA200204553A ZA200204553A ZA200204553B ZA 200204553 B ZA200204553 B ZA 200204553B ZA 200204553 A ZA200204553 A ZA 200204553A ZA 200204553 A ZA200204553 A ZA 200204553A ZA 200204553 B ZA200204553 B ZA 200204553B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- alkyl
- group
- compound
- amino
- Prior art date
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- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title description 4
- 230000000694 effects Effects 0.000 title description 4
- 150000003672 ureas Chemical class 0.000 title description 3
- 239000003149 muscarinic antagonist Substances 0.000 title description 2
- -1 amino, substituted amino Chemical group 0.000 claims description 130
- 125000000217 alkyl group Chemical group 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 63
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 58
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 46
- 125000005647 linker group Chemical group 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 125000002252 acyl group Chemical group 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 19
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 19
- 125000004442 acylamino group Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 16
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 16
- 125000004470 heterocyclooxy group Chemical group 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
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- 125000005296 thioaryloxy group Chemical group 0.000 claims description 15
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- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 229930194542 Keto Natural products 0.000 claims description 13
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 13
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- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 13
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- 125000005255 oxyaminoacyl group Chemical group 0.000 claims description 13
- 125000005323 thioketone group Chemical group 0.000 claims description 13
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 229910020008 S(O) Inorganic materials 0.000 claims description 11
- 125000004476 heterocycloamino group Chemical group 0.000 claims description 11
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 9
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003446 ligand Substances 0.000 claims description 8
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- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
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- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 6
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
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- 208000008630 Sialorrhea Diseases 0.000 claims 2
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- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
- NBXKUSNBCPPKRA-UHFFFAOYSA-N 1,4,7,10,13-pentaoxa-16-azacyclooctadecane Chemical compound C1COCCOCCOCCOCCOCCN1 NBXKUSNBCPPKRA-UHFFFAOYSA-N 0.000 claims 1
- BJUOQSZSDIHZNP-UHFFFAOYSA-N 1,4,7,10-tetraoxa-13-azacyclopentadecane Chemical compound C1COCCOCCOCCOCCN1 BJUOQSZSDIHZNP-UHFFFAOYSA-N 0.000 claims 1
- VUCWMAJEUOWLEY-UHFFFAOYSA-N 1-$l^{1}-azanylpiperidine Chemical compound [N]N1CCCCC1 VUCWMAJEUOWLEY-UHFFFAOYSA-N 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 210000003079 salivary gland Anatomy 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
Classifications
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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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
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- C07—ORGANIC CHEMISTRY
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/14—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 three or more hetero rings
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- 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
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- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
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US45617099A | 1999-12-07 | 1999-12-07 |
Publications (1)
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ZA200204553B true ZA200204553B (en) | 2003-09-08 |
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ZA200204553A ZA200204553B (en) | 1999-12-07 | 2002-06-06 | Urea compounds having muscarinic receptor antagonist activity. |
ZA200204557A ZA200204557B (en) | 1999-12-07 | 2002-06-06 | Carbamate derivatives having muscarinic receptor antagonist activity. |
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ZA200204557A ZA200204557B (en) | 1999-12-07 | 2002-06-06 | Carbamate derivatives having muscarinic receptor antagonist activity. |
Country Status (27)
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US (3) | US6635764B2 (fr) |
EP (2) | EP1235803B1 (fr) |
JP (1) | JP2003516391A (fr) |
KR (1) | KR100748150B1 (fr) |
CN (1) | CN1271054C (fr) |
AT (2) | ATE439345T1 (fr) |
AU (1) | AU782232B2 (fr) |
BR (1) | BR0015963A (fr) |
CA (1) | CA2392030C (fr) |
CZ (1) | CZ20021830A3 (fr) |
DE (2) | DE60042762D1 (fr) |
EA (1) | EA006437B1 (fr) |
ES (3) | ES2329785T3 (fr) |
HK (1) | HK1049483B (fr) |
HR (1) | HRP20020574B1 (fr) |
HU (1) | HUP0203677A2 (fr) |
IL (2) | IL149289A0 (fr) |
IS (1) | IS2191B (fr) |
MX (1) | MXPA02005602A (fr) |
NO (1) | NO323544B1 (fr) |
NZ (1) | NZ518722A (fr) |
PL (1) | PL364922A1 (fr) |
SK (1) | SK7982002A3 (fr) |
UA (1) | UA73543C2 (fr) |
WO (1) | WO2001042213A1 (fr) |
YU (1) | YU42402A (fr) |
ZA (2) | ZA200204553B (fr) |
Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA73543C2 (uk) * | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
GB0108099D0 (en) * | 2001-03-30 | 2001-05-23 | Hoffmann La Roche | Aminopiperidine derivatives |
US20030236287A1 (en) * | 2002-05-03 | 2003-12-25 | Piotrowski David W. | Positive allosteric modulators of the nicotinic acetylcholine receptor |
CA2492121A1 (fr) | 2002-07-08 | 2004-01-15 | Ranbaxy Laboratories Limited | Derives d'azabicyclo[3.1.0]hexanes 3,6-disubstitues utiles comme antagonistes des recepteurs muscariniques |
TW200800953A (en) * | 2002-10-30 | 2008-01-01 | Theravance Inc | Intermediates for preparing substituted 4-amino-1-(pyridylmethyl) piperidine |
CN100364990C (zh) * | 2002-10-30 | 2008-01-30 | 施万制药 | 取代的4-氨基-1-(吡啶甲基)哌啶和相关化合物 |
PE20040950A1 (es) * | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
CN101239971B (zh) * | 2003-02-14 | 2011-07-20 | 施万制药 | 联苯衍生物 |
US20050026844A1 (en) | 2003-04-03 | 2005-02-03 | Regents Of The University Of California | Inhibitors for the soluble epoxide hydrolase |
US7517905B2 (en) | 2003-04-09 | 2009-04-14 | Ranbaxy Laboratories Limited | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
JP2006522787A (ja) | 2003-04-11 | 2006-10-05 | ランバクシー ラボラトリーズ リミテッド | ムスカリン様受容体アンタゴニストとしてのアザビシクロ誘導体 |
JP2007518677A (ja) * | 2003-06-23 | 2007-07-12 | シーブイ・セラピューティクス・インコーポレイテッド | 脂肪酸酸化インヒビターとしてのピペラジンおよびピペリジンのウレア誘導体 |
US7368463B2 (en) * | 2003-07-11 | 2008-05-06 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
AR047759A1 (es) * | 2003-09-26 | 2006-02-22 | Vertex Pharma | Derivados de fenil - piperazina como moduladores de receptores muscarnicos |
PE20050973A1 (es) * | 2003-10-29 | 2005-11-19 | Theravance Inc | Sales de acido naftalen-1,5-disulfonico de un compuesto de 4-amino-1-(piridilmetil)piperidina como antagonistas de receptores muscarinicos |
DE602004021959D1 (de) | 2003-11-21 | 2009-08-20 | Theravance Inc | Verbindungen mit agonistischer wirkung am beta2-adrenergen rezeptor und am muscarinischen rezeptor |
WO2005080375A1 (fr) * | 2004-02-13 | 2005-09-01 | Theravance, Inc. | Cristalline d'un compose biphenyle |
TWI341836B (en) | 2004-03-11 | 2011-05-11 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
EP1723113A1 (fr) * | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Composes biphenyle convenant en tant qu'antagonistes du recepteur muscarinique |
JP2007528416A (ja) * | 2004-03-11 | 2007-10-11 | セラヴァンス, インコーポレーテッド | ムスカリンレセプターアンタゴニストとしての有用なビフェニル化合物 |
EP1723115A1 (fr) * | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Composes de biphenyle utiles comme antagonistes du recepteur muscarinique |
EP1723108A1 (fr) * | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Composes biphenyle utiles comme antagonistes du recepteur muscarinique |
JP2007528408A (ja) * | 2004-03-11 | 2007-10-11 | セラヴァンス, インコーポレーテッド | ムスカリンレセプターアンタゴニストとしての有用なビフェニル化合物 |
TW200538095A (en) * | 2004-03-11 | 2005-12-01 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
US7501442B2 (en) * | 2004-03-11 | 2009-03-10 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
CA2559665A1 (fr) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reduction de la nephropathie au moyen d'inhibiteurs d'hydrolase d'epoxyde soluble et d'epoxyeicosanoides |
JP2008500398A (ja) * | 2004-05-21 | 2008-01-10 | ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア | Wnt阻害因子−1(WIF−1)で癌を処置および診断するための方法 |
US7528253B2 (en) * | 2004-08-16 | 2009-05-05 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
JP2008510015A (ja) | 2004-08-16 | 2008-04-03 | セラヴァンス, インコーポレーテッド | β2アドレナリン作用性レセプターアゴニスト活性およびムスカリン性レセプターアンタゴニスト活性を有する化合物 |
TWI374883B (en) | 2004-08-16 | 2012-10-21 | Theravance Inc | Crystalline form of a biphenyl compound |
CA2584342C (fr) * | 2004-10-20 | 2013-04-30 | The Regents Of The University Of California | Inhibiteurs ameliores de l'epoxyde hydrolase soluble |
US7880007B2 (en) * | 2004-11-29 | 2011-02-01 | Vertex Pharmaceuticals Incorporated | Bicyclic substituted phenyl piperidine modulators of muscarinic receptors |
GB0503054D0 (en) * | 2005-02-14 | 2005-03-23 | Smithkline Beecham Corp | Chemical compounds |
TW200714587A (en) * | 2005-03-10 | 2007-04-16 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
JP2008537931A (ja) * | 2005-03-10 | 2008-10-02 | セラヴァンス, インコーポレーテッド | ムスカリン性レセプターアンタゴニストとして有用なビフェニル化合物 |
JP2008538104A (ja) * | 2005-03-10 | 2008-10-09 | セラヴァンス, インコーポレーテッド | ムスカリン受容体アンタゴニストとして有用なビフェニル化合物 |
TWI372749B (en) * | 2005-03-10 | 2012-09-21 | Theravance Inc | Crystalline forms of a biphenyl compound |
US7659403B2 (en) * | 2005-03-10 | 2010-02-09 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
WO2006099032A1 (fr) * | 2005-03-10 | 2006-09-21 | Theravance, Inc. | Composes de biphenyle utilises comme antagonistes des recepteurs muscariniques |
EP1863490A2 (fr) * | 2005-03-28 | 2007-12-12 | Vertex Pharmaceuticals Incorporated | Modulateurs muscariniques |
JP2008546695A (ja) | 2005-06-13 | 2008-12-25 | セラヴァンス, インコーポレーテッド | ムスカリン受容体アンタゴニストとして有用なビフェニル化合物 |
US8429052B2 (en) * | 2005-07-19 | 2013-04-23 | Lincoln National Life Insurance Company | Method and system for providing employer-sponsored retirement plan |
RU2008119323A (ru) | 2005-10-19 | 2009-11-27 | Рэнбакси Лабораториз Лимитед (In) | Фармацевтические композиции мускаринового рецептора |
GB0602778D0 (en) * | 2006-02-10 | 2006-03-22 | Glaxo Group Ltd | Novel compound |
US7973055B2 (en) * | 2006-03-09 | 2011-07-05 | Theravance, Inc. | Crystalline forms of a biphenyl compound |
TW200808723A (en) * | 2006-03-13 | 2008-02-16 | Univ California | Conformationally restricted urea inhibitors of soluble epoxide hydrolase |
KR20090107567A (ko) | 2007-02-09 | 2009-10-13 | 아스텔라스세이야쿠 가부시키가이샤 | 아자 가교환 화합물 |
WO2009079392A1 (fr) * | 2007-12-14 | 2009-06-25 | Theravance, Inc. | Composés contenant de l'amidine utiles comme antagonistes du récepteur muscarinique |
EP2096105A1 (fr) * | 2008-02-28 | 2009-09-02 | Laboratorios Almirall, S.A. | Dérivés de 4-(2-amino-1-hydroxyethyl)phénol en tant qu'antagonistes du récepteur adrénergique b2 |
NZ595850A (en) | 2009-04-23 | 2013-05-31 | Theravance Inc | DIAMIDE COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND Beta2 ADRENERGIC RECEPTOR AGONIST ACTIVITY |
US9296693B2 (en) | 2010-01-29 | 2016-03-29 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
KR20130140672A (ko) * | 2010-10-20 | 2013-12-24 | 키에시 파르마슈티시 엣스. 피. 에이. | 기침 치료용 카보네이트 유도체 |
JP6021616B2 (ja) * | 2012-12-04 | 2016-11-09 | 株式会社アエタスファルマ | 3−ピペラジニル−1−ピペリジニル−プロパン誘導体及びそれを含有してなる医薬組成物 |
KR101514320B1 (ko) | 2013-06-14 | 2015-04-22 | 재단법인 의약바이오컨버젼스연구단 | 신규한 암 예방 또는 치료용 약학적 조성물 |
PT3153511T (pt) * | 2014-06-06 | 2019-06-28 | Astellas Pharma Inc | Derivado de 2-acilaminotiazole para utilização na prevenção ou tratamento de doenças da bexiga/trato urinário |
WO2020086864A1 (fr) * | 2018-10-24 | 2020-04-30 | Vanderbilt University | Modulateurs allostériques positifs du récepteur d'acétylcholine muscarinique m1 |
WO2020204548A1 (fr) * | 2019-03-29 | 2020-10-08 | 재단법인 의약바이오컨버젼스연구단 | Nouveau composé ayant une activité anticancéreuse, et procédé de production associé |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4587046A (en) | 1982-05-18 | 1986-05-06 | The Regents Of The University Of California | Drug-carrier conjugates |
DE3402060A1 (de) | 1984-01-21 | 1985-08-01 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
US4675326A (en) | 1985-05-08 | 1987-06-23 | Gabriel Amitai | Bisquaternary antidotes |
DK443489D0 (da) | 1989-09-08 | 1989-09-08 | Ferrosan As | Substituerede urinstofforbindelser, deres fremstilling og anvendelse |
NZ251687A (en) * | 1992-03-31 | 1995-12-21 | Glaxo Group Ltd | Oxadiazol- and thiadiazol- phenylcarbamates and -phenylureas and pharmaceutical compositions thereof |
CA2123728A1 (fr) * | 1993-05-21 | 1994-11-22 | Noriyoshi Sueda | Derives de l'uree et leur utilisation comme inhibiteurs de l'acat |
AU7545894A (en) | 1993-09-02 | 1995-03-22 | Yamanouchi Pharmaceutical Co., Ltd. | Carbamate derivative and medicine containing the same |
AU685225B2 (en) | 1994-02-10 | 1998-01-15 | Yamanouchi Pharmaceutical Co., Ltd. | Novel carbamate derivative and medicinal composition containing the same |
US5691323A (en) | 1995-05-12 | 1997-11-25 | Merck & Co., Inc. | Muscarine antagonists |
WO1997013766A1 (fr) * | 1995-10-13 | 1997-04-17 | Banyu Pharmaceutical Co., Ltd. | Derives heteroaromatiques substitues |
EP0923374A1 (fr) * | 1996-07-01 | 1999-06-23 | Sepracor, Inc. | Procedes et compositions de traitement de l'incontinence urinaire par (s)-trihexyphenidyle enrichi en enantiomere |
US6500934B1 (en) | 1996-07-24 | 2002-12-31 | Michael Rush Lerner | Bivalent agonists for G-protein coupled receptors |
PE92198A1 (es) | 1996-08-01 | 1999-01-09 | Banyu Pharma Co Ltd | Derivados de 1,4-piperidina disustituida que contienen fluor |
US6062766A (en) * | 1997-08-04 | 2000-05-16 | Quixote Corporation | Raised pavement marker |
JP2002508366A (ja) * | 1997-12-12 | 2002-03-19 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | キノリンピペラジンおよびキノリンピペリジン誘導体、それらの製造方法、ならびに複合的5−ht1a、5−ht1bおよび5−ht1d受容体アンタゴニストとしてのそれらの用途 |
US6086881A (en) * | 1998-05-15 | 2000-07-11 | Children's Medical Center Corp. | Spatially aligned conjugated composition having a thioether bond linkage |
US6066636A (en) * | 1998-06-30 | 2000-05-23 | Schering Corporation | Muscarinic antagonists |
MXPA02005596A (es) * | 1999-12-07 | 2004-09-10 | Theravance Inc | Derivados de carbamato con actividad antagonista para el rerceptor muscarinico. |
UA73543C2 (uk) * | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
WO2001098458A2 (fr) * | 2000-06-19 | 2001-12-27 | Zyomyx, Inc. | Procédés permettant d'immobiliser des polypeptides |
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2000
- 2000-07-12 UA UA2002075566A patent/UA73543C2/uk unknown
- 2000-12-07 EP EP00982493A patent/EP1235803B1/fr not_active Expired - Lifetime
- 2000-12-07 ES ES04012859T patent/ES2329785T3/es not_active Expired - Lifetime
- 2000-12-07 AU AU19518/01A patent/AU782232B2/en not_active Expired
- 2000-12-07 DE DE60042762T patent/DE60042762D1/de not_active Expired - Lifetime
- 2000-12-07 DE DE60012223T patent/DE60012223T2/de not_active Expired - Lifetime
- 2000-12-07 CZ CZ20021830A patent/CZ20021830A3/cs unknown
- 2000-12-07 SK SK798-2002A patent/SK7982002A3/sk unknown
- 2000-12-07 WO PCT/US2000/033155 patent/WO2001042213A1/fr not_active Application Discontinuation
- 2000-12-07 MX MXPA02005602A patent/MXPA02005602A/es active IP Right Grant
- 2000-12-07 EP EP04012859A patent/EP1457488B1/fr not_active Expired - Lifetime
- 2000-12-07 ES ES00982493T patent/ES2225275T3/es not_active Expired - Lifetime
- 2000-12-07 ES ES00983991T patent/ES2243333T3/es not_active Expired - Lifetime
- 2000-12-07 EA EA200200646A patent/EA006437B1/ru not_active IP Right Cessation
- 2000-12-07 JP JP2001543514A patent/JP2003516391A/ja active Pending
- 2000-12-07 CN CNB008167028A patent/CN1271054C/zh not_active Expired - Lifetime
- 2000-12-07 AT AT04012859T patent/ATE439345T1/de not_active IP Right Cessation
- 2000-12-07 NZ NZ518722A patent/NZ518722A/en not_active IP Right Cessation
- 2000-12-07 IL IL14928900A patent/IL149289A0/xx active IP Right Grant
- 2000-12-07 HU HU0203677A patent/HUP0203677A2/hu unknown
- 2000-12-07 AT AT00982493T patent/ATE271039T1/de not_active IP Right Cessation
- 2000-12-07 KR KR1020027007147A patent/KR100748150B1/ko active IP Right Grant
- 2000-12-07 PL PL00364922A patent/PL364922A1/xx not_active Application Discontinuation
- 2000-12-07 CA CA002392030A patent/CA2392030C/fr not_active Expired - Lifetime
- 2000-12-07 BR BR0015963-8A patent/BR0015963A/pt not_active Application Discontinuation
- 2000-12-07 YU YU42402A patent/YU42402A/sh unknown
- 2000-12-07 US US09/732,514 patent/US6635764B2/en not_active Expired - Lifetime
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2002
- 2002-04-23 IL IL149289A patent/IL149289A/en unknown
- 2002-04-26 IS IS6362A patent/IS2191B/is unknown
- 2002-06-06 NO NO20022683A patent/NO323544B1/no not_active IP Right Cessation
- 2002-06-06 ZA ZA200204553A patent/ZA200204553B/en unknown
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- 2002-07-04 HR HR20020574A patent/HRP20020574B1/xx not_active IP Right Cessation
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2003
- 2003-03-03 HK HK03101572.1A patent/HK1049483B/zh not_active IP Right Cessation
- 2003-04-30 US US10/426,364 patent/US20040054187A1/en not_active Abandoned
- 2003-04-30 US US10/426,270 patent/US20040116706A1/en not_active Abandoned
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