http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-039367-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_966a6c1f382ec9bcb5e3839dfd73e5b8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P11-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P11-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D417-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D417-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P31-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-30 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-34 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-36 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P29-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P37-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P43-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P11-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P11-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-4439 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P29-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P43-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D417-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P37-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D417-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-34 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-36 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-5377 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P9-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P9-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P25-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P9-00 |
| filingDate | 2002-11-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_209259f9f93ce12923b6dae8f91c4a70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_45590828fce09c7cdec31e2339d1a132 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0ab77634fa1c5c10678b83b5aa3f78f8 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_1f420c5a22a29e9093f14e38f2f83a76 |
| publicationDate | 2005-02-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-039367-A1 |
| titleOfInvention | COMPOUNDS DERIVED FROM BENZOTIAZOL, NICOTINE OR ISONICOTINE, A PROCESS FOR THEIR PREPARATION, A MEDICINAL PRODUCT THAT CONTAINS AND USE THEMSELVES |
| abstract | Compounds derived from benzothiazole nicotine or isonicotine of the general formula (1) or (2), wherein: R1 is phenyl, piperidin-1-yl or morpholinyl; A is -O-; and R is - (CH2) nN (R '') - C (O) - lower alkyl, - (C2) nO-lower alkyl, - (CH2) nO- (CH2) nO-lower alkyl, lower alkyl, - ( CH2) n-morpholinyl, - (CH2) n-phenyl, - (CH2) nN (R '') 2, - (CH2) n-pyridinyl, - (CH2) n-CF3, - (CH2) n-2- oxo-pyrrolidinyl or C4-6 cycloalkyl; R '' is independently from each other hydrogen or lower alkyl and n is 1 or 2; or A is -N (R ') -; and R is lower alkyl, C4-6 cycloalkyl, - (CH2) nO-lower alkyl, - (CH2) n-pyridinyl, - (CH2) n-piperidinyl, - (CH2) n-phenyl, - (CH2) nN ( R '') - C (O) - lower alkyl, - (CH2) n-morpholinyl, or - (CH2) nN (R '') 2; R 'and R' 'are independently of each other hydrogen or lower alkyl and n is 1 or 2; or A is -CH2-; and R is -N (R '') - (CH2) mO-lower alkyl, -N (R '') 2, S-lower alkyl, or is acetidinyl, pyrrolidinyl or piperidinyl, which are optionally substituted by hydroxyl or lower alkoxy or is morpholinyl, -N (R '') - (CH2) m-C4-6 cycloalkyl, -N (R '') - (CH2) mC (O) O-lower alkyl, -N (R '') - (CH2) mC (O) OH, -2-oxo-pyrrolidinyl, -N (R '') -C (O) O-lower alkyl, -O (CH2) mO-lower alkyl or alkoxy; R '' is independently from each other hydrogen or lower alkyl and m is 1, 2 or 3; or A is -S-; and R is lower alkyl; or AR are together -piperazinyl, substituted by lower alkyl, -C (O) -alkyl or an oxo group, or is piperidinyl, substituted by lower alkoxy or hydroxy, or is morpholinyl, substituted by lower alkyl, or is C4-cycloalkyl- 6, -azetidin-1-yl, optionally substituted by hydroxyl or lower alkoxy, thiomorpholin-1,1-dioxo-tetrahydropyran or 2-oxa-5-aza-bicyclo [2.2.1] hept-5-yl; and pharmaceutically acceptable salts thereof. It has been found that the compounds of the general formula (1) are linked to the adenosine receptor. Specifically, these compounds have a good affinity for the adenosine A2A receptor and these are therefore useful in the treatment of diseases related to this receptor. These compounds are useful in the control or prevention of diseases based on the modulation of the adenosine system, such as Alzheimer's disease, Parkinson's disease, Huntington's disease, neuroprotection, schizophrenia, anxiety, pain, respiratory deficits, depression , drug addiction, such as amphetamines, cocaine, opioids, ethanol, nicotine, cannabinoids or asthma, allergic responses, hypoxia, ischemia, seizures and substance abuse. In addition, these compounds could be useful as sedatives, muscle relaxants, antipsychotics, antiepileptics, anticonvulsants and cardioprotective agents against disorders such as coronary artery disease and cardiac arrest. The most preferable indications according to the present are those, which are based on the antagonistic activity of the A2A receptor and which include disorders of the central nervous system, for example the treatment or prevention of Alzheimer's disease, certain depressive disorders, addition to the drugs, neuroprotection and Parkinson's disease as well as ADHD. A process for its preparation, a medicine that contains them and their use are also disclosed. Claim 34: A process for the preparation of a compound of formula (1) or (2) as defined in claim 1, which process comprises: a) reaction of a compound of formula (3) or (4) with a compound of formula: HAR, in the presence of a base to give a compound of formula (1) or (2) wherein R is - (CH2) nN (R '') - C (O) - lower alkyl, - (CH2 ) nO-lower alkyl, - (CH2) nO- (CH2) nO-lower alkyl, lower alkyl, - (CH2) n-morpholinyl, - (CH2) n-phenyl, - (CH2) nN (R '') 2 , - (CH2) n-pyridinyl, - (CH2) n-CF3, - (CH2) n-2-oxo-pyrrolidinyl or CH4-6-cycloalkyl, Y is chlorine or bromine, A is oxygen or sulfur, and n is 1 or 2; b) reaction of a compound of formula (3) or (4) with a compound of formula HNRR 'to give a compound of formula (5) or (6) wherein R is lower alkyl, C4-6 cycloalkyl, - (CH2 ) nO-lower alkyl, - (CH2) n-pyridinyl, - (CH2) n-piperidinyl, - (CH2) n-phenyl, - (CH2) nN (R '') - C (O) - lower alkyl, - (CH2) n-morpholinyl or - (CH2) nN (R '') 2 or R and R 'together with the N atom form the following groups: piperazinyl, optionally substituted with lower alkyl, C (O) -alkyl lower or an oxo, piperidinyl group, optionally substituted by lower alkoxy or hydroxyl, morpholinyl, optionally substituted by lower alkyl, azetidin-1-yl, optionally substituted by hydroxyl or lower alkoxy, or thiomorpholin-1,1-dioxo or 2-oxa-bicyclo [2.21] hept-5-yl, R 'and R' 'are independently from each other hydrogen or lower alkyl, Y is chlorine or bromine and n is 1 or 2; or c) reaction of a compound of formula (7) or (8) with a compound of formula HR to give a compound of formula (9) or (10) wherein R is -N (R '') - (C2) mO-lower alkyl, -N (R '') 2, -S-lower alkyl or is acetidinyl, pyrrolidinyl or piperidinyl, which are optionally substituted by hydroxyl or lower alkoxy or is morpholinyl, -N (R '') - (CH2 ) m- (C4-6 cycloalkyl), N (R '') - (CH2) mC (O) O-lower alkyl, -N (R '') - (CH2) mC (O) OH, -2-oxo -pyrrolidinyl, -N (R '') - C (O) O-lower alkyl, -O (CH2) mO-lower alkyl or alkoxy, R '' is independently of each other hydrogen or lower alkyl and m is 1, 2 or 3, od) reaction of a compound of formula (7) or (8) with a compound of formula HOR to give a compound of formula (11) or (12) wherein R is - (CH2) mO-lower alkyl or is lower alkyl and m is 1, 2 or 3, or e) reaction of a compound of formula (3) or (4) with a compound of formula Bu3Sn-A'-R / cat or with B (OH) 2-A'- R / cat to give a compound of formula (13) or (14) wherein A'-R are together C4-6 cycloalkenyl or dihidopyran and Y is bromine, and then reacting a compound of formula (13) or (14) with hydrogen and a catalyst to give the compound of formula (1) or (2) wherein AR are together C4-6 cycloalkyl or tetrahydropyran, and if desired, convert the compounds obtained into pharmaceutically acceptable acid addition salts. |
| priorityDate | 2001-11-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 101.