OA13270A - Muscarinic acetylcholine receptor antagonists. - Google Patents

Muscarinic acetylcholine receptor antagonists. Download PDF

Info

Publication number: OA13270A
Authority: OA; OAPI
Prior art keywords: bicyclo; hydroxy; azonia; compound; dimethyl
Prior art date: 2003-10-17

Application number

OA1200600124A

Other languages

English (en)

Inventor

Michael R Palovich

Zehong Wan

Chongjie Zhu

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

2003-10-17

Filing date

2004-10-15

Publication date

2007-01-31

2004-10-15 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2007-01-31 Publication of OA13270A publication Critical patent/OA13270A/en

Links

229940121683 Acetylcholine receptor antagonist Drugs 0.000 title abstract description 3
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title abstract description 3
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims description 31
102000005962 receptors Human genes 0.000 claims description 12
108020003175 receptors Proteins 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
230000001404 mediated effect Effects 0.000 claims description 7
230000003551 muscarinic effect Effects 0.000 claims description 7
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
BUFDXBRKTDFWRN-UHFFFAOYSA-M 2-(8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-ylidene)-1,1-dithiophen-2-ylethanol;iodide Chemical compound [I-].C[N+]1(C)C(C2)CCC1CC2=CC(O)(C=1SC=CC=1)C1=CC=CS1 BUFDXBRKTDFWRN-UHFFFAOYSA-M 0.000 claims description 4
NIFBNIANYCOETB-UHFFFAOYSA-N 8-methyl-n-(2-phenylethyl)-8-azabicyclo[3.2.1]octan-3-amine Chemical compound CN1C(C2)CCC1CC2NCCC1=CC=CC=C1 NIFBNIANYCOETB-UHFFFAOYSA-N 0.000 claims description 3
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
NPVWDHNHELWOAT-UHFFFAOYSA-M 2-(8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-ylidene)-1,1-diphenylethanol;iodide Chemical compound [I-].C[N+]1(C)C(C2)CCC1CC2=CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 NPVWDHNHELWOAT-UHFFFAOYSA-M 0.000 claims description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229940077388 benzenesulfonate Drugs 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
229940112141 dry powder inhaler Drugs 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
PQZAQCOGMGANAE-UHFFFAOYSA-M 2-benzyl-1-(8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-ylidene)-3-phenylpropan-2-ol;iodide Chemical compound [I-].C[N+]1(C)C(C2)CCC1CC2=CC(O)(CC=1C=CC=CC=1)CC1=CC=CC=C1 PQZAQCOGMGANAE-UHFFFAOYSA-M 0.000 claims 1
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206010014561 Emphysema Diseases 0.000 claims 1
206010061876 Obstruction Diseases 0.000 claims 1
JVMKZHYSVDTFED-UHFFFAOYSA-N bicyclo[3.2.1]octane hydroiodide Chemical compound I.C1C2CCC1CCC2 JVMKZHYSVDTFED-UHFFFAOYSA-N 0.000 claims 1
206010006451 bronchitis Diseases 0.000 claims 1
208000007451 chronic bronchitis Diseases 0.000 claims 1
229940071648 metered dose inhaler Drugs 0.000 claims 1
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238000000034 method Methods 0.000 abstract description 10
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
-1 ammonium cations Chemical class 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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AMJRSUWJSRKGNO-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-5-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)phenoxy]ethoxy]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O AMJRSUWJSRKGNO-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 3
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230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
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150000001768 cations Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
125000004446 heteroarylalkyl group Chemical group 0.000 description 2
125000005343 heterocyclic alkyl group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000003068 molecular probe Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
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229960002510 mandelic acid Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
OXBRQNQURPPYHW-UHFFFAOYSA-N methyl 2-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetate Chemical compound C1C(=CC(=O)OC)CC2CCC1N2C OXBRQNQURPPYHW-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000008569 process Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
230000007384 vagal nerve stimulation Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- 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
- A61P11/06—Antiasthmatics
- 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
- A61P11/08—Bronchodilators
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Otolaryngology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

OA1200600124A 2003-10-17 2004-10-15 Muscarinic acetylcholine receptor antagonists. OA13270A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US51216103P	2003-10-17	2003-10-17

Publications (1)

Publication Number	Publication Date
OA13270A true OA13270A (en)	2007-01-31

Family

ID=34465319

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200600124A OA13270A (en)	2003-10-17	2004-10-15	Muscarinic acetylcholine receptor antagonists.

Country Status (22)

Country	Link
US (1)	US7507747B2 (is)
EP (1)	EP1677796A4 (is)
JP (1)	JP2007509061A (is)
CN (1)	CN1897947A (is)
AP (1)	AP2006003575A0 (is)
AR (1)	AR046114A1 (is)
AU (1)	AU2004281167A1 (is)
BR (1)	BRPI0415281A (is)
CA (1)	CA2542636A1 (is)
EA (1)	EA200600787A1 (is)
EC (1)	ECSP066486A (is)
IL (1)	IL174846A0 (is)
IS (1)	IS8440A (is)
MA (1)	MA28109A1 (is)
MX (1)	MXPA06004242A (is)
NO (1)	NO20062071L (is)
OA (1)	OA13270A (is)
PE (1)	PE20050442A1 (is)
TW (1)	TW200528448A (is)
UY (1)	UY28567A1 (is)
WO (1)	WO2005037224A2 (is)
ZA (1)	ZA200602783B (is)

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2004
- 2004-10-15 EP EP04795406A patent/EP1677796A4/en not_active Withdrawn
- 2004-10-15 CA CA002542636A patent/CA2542636A1/en not_active Abandoned
- 2004-10-15 UY UY28567A patent/UY28567A1/es not_active Application Discontinuation
- 2004-10-15 AR ARP040103734A patent/AR046114A1/es not_active Application Discontinuation
- 2004-10-15 AP AP2006003575A patent/AP2006003575A0/xx unknown
- 2004-10-15 AU AU2004281167A patent/AU2004281167A1/en not_active Abandoned
- 2004-10-15 WO PCT/US2004/034234 patent/WO2005037224A2/en not_active Ceased
- 2004-10-15 MX MXPA06004242A patent/MXPA06004242A/es not_active Application Discontinuation
- 2004-10-15 CN CNA2004800380467A patent/CN1897947A/zh active Pending
- 2004-10-15 US US10/575,837 patent/US7507747B2/en not_active Expired - Fee Related
- 2004-10-15 OA OA1200600124A patent/OA13270A/en unknown
- 2004-10-15 BR BRPI0415281-6A patent/BRPI0415281A/pt not_active Application Discontinuation
- 2004-10-15 TW TW093131251A patent/TW200528448A/zh unknown
- 2004-10-15 JP JP2006535384A patent/JP2007509061A/ja active Pending
- 2004-10-15 PE PE2004001004A patent/PE20050442A1/es not_active Application Discontinuation
- 2004-10-15 EA EA200600787A patent/EA200600787A1/ru unknown
2006
- 2006-04-05 ZA ZA200602783A patent/ZA200602783B/xx unknown
- 2006-04-06 EC EC2006006486A patent/ECSP066486A/es unknown
- 2006-04-06 IL IL174846A patent/IL174846A0/en unknown
- 2006-04-25 MA MA28963A patent/MA28109A1/fr unknown
- 2006-05-05 IS IS8440A patent/IS8440A/is unknown
- 2006-05-08 NO NO20062071A patent/NO20062071L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
AR046114A1 (es)	2005-11-23
EP1677796A2 (en)	2006-07-12
UY28567A1 (es)	2005-05-31
JP2007509061A (ja)	2007-04-12
IS8440A (is)	2006-05-05
BRPI0415281A (pt)	2006-12-19
AP2006003575A0 (en)	2006-04-30
EP1677796A4 (en)	2006-12-27
US7507747B2 (en)	2009-03-24
MA28109A1 (fr)	2006-08-01
EA200600787A1 (ru)	2006-08-25
IL174846A0 (en)	2006-08-20
WO2005037224A2 (en)	2005-04-28
AU2004281167A1 (en)	2005-04-28
PE20050442A1 (es)	2005-07-09
MXPA06004242A (es)	2006-06-28
CA2542636A1 (en)	2005-04-28
NO20062071L (no)	2006-05-08
ECSP066486A (es)	2006-10-10
CN1897947A (zh)	2007-01-17
TW200528448A (en)	2005-09-01
US20070135478A1 (en)	2007-06-14
WO2005037224A3 (en)	2005-06-23
ZA200602783B (en)	2007-11-28

Publication	Publication Date	Title
OA13316A (en)	2007-04-13	Muscarinic acetylcholine receptor antagonists.
US7507747B2 (en)	2009-03-24	Muscarinic acetylcholine receptor antagonists
TW200524577A (en)	2005-08-01	Muscarinic acetylcholine receptor antagonists
JP2006502180A (ja)	2006-01-19	５−ｈｔ４レセプターモジュレーターとしてのｎ−置換されたピペリジニル−イミダゾピリジン化合物
AU2011268373B2 (en)	2014-05-22	Piperidinyl compound as a modulator of chemokine receptor activity
EP2121688A1 (en)	2009-11-25	Heterocyclic derivatives as m3 muscarinic receptors
WO2006065788A2 (en)	2006-06-22	Novel muscarinic acetylcholine receptor antagonists
PT1960398E (pt)	2010-11-26	Derivados de ácido e de ésteres arilacéticos e suas utilizações como anti-inflamatórios
JPH0761968A (ja)	1995-03-07	ヘテロ環を含有する尿素誘導体
AU2018215466B2 (en)	2022-03-10	Small molecule antagonists of SUMO related modification of CRMP2 and uses thereof
AU2007203077B2 (en)	2010-07-22	Muscarinic acetylcholine receptor antagonists
KR20070017965A (ko)	2007-02-13	무스카린성 아세틸콜린 수용체 길항제
WO2025184322A1 (en)	2025-09-04	Heterocyclic compounds and methods of use thereof