ZA200303640B - Substituted 3.4-dihydro-pyrido[1,2-A]pyrimidines. - Google Patents

Substituted 3.4-dihydro-pyrido[1,2-A]pyrimidines. Download PDF

Info

Publication number: ZA200303640B
Authority: ZA; South Africa
Prior art keywords: alkyl; polysubstituted; unsubstituted; mono; aryl
Prior art date: 2000-10-13

Application number

ZA200303640A

Other languages

English (en)

Inventor

Matthias Gerlach

Utz-Peter Jagusch

Corinna-Nee-Maul Sundermann

Original Assignee

Gruenenthal Gmbh

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.)

2000-10-13

Filing date

2003-05-12

Publication date

2004-08-12

2003-05-12 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

2004-08-12 Publication of ZA200303640B publication Critical patent/ZA200303640B/en

Links

150000003230 pyrimidines Chemical class 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims description 611
125000003118 aryl group Chemical group 0.000 claims description 373
229920006395 saturated elastomer Polymers 0.000 claims description 308
125000001072 heteroaryl group Chemical group 0.000 claims description 175
125000000753 cycloalkyl group Chemical group 0.000 claims description 152
150000001875 compounds Chemical class 0.000 claims description 99
229910052799 carbon Inorganic materials 0.000 claims description 78
125000004432 carbon atom Chemical group C* 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 59
125000000623 heterocyclic group Chemical group 0.000 claims description 36
-1 COzH Chemical group 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
208000002193 Pain Diseases 0.000 claims description 10
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
206010012735 Diarrhoea Diseases 0.000 claims description 3
208000003251 Pruritus Diseases 0.000 claims description 3
208000009205 Tinnitus Diseases 0.000 claims description 3
206010046543 Urinary incontinence Diseases 0.000 claims description 3
PYFMAAFCQDFHJX-UHFFFAOYSA-N ethyl pyrimidine-2-carboxylate Chemical compound CCOC(=O)C1=NC=CC=N1 PYFMAAFCQDFHJX-UHFFFAOYSA-N 0.000 claims description 3
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 claims description 3
231100000886 tinnitus Toxicity 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims 8
150000001336 alkenes Chemical class 0.000 claims 4
125000005241 heteroarylamino group Chemical group 0.000 claims 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
229910052796 boron Inorganic materials 0.000 claims 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
150000001299 aldehydes Chemical class 0.000 claims 2
239000003960 organic solvent Substances 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
230000035484 reaction time Effects 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 description 9
125000003342 alkenyl group Chemical group 0.000 description 6
125000000304 alkynyl group Chemical group 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000000094 Chronic Pain Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
125000005213 alkyl heteroaryl group Chemical group 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
206010010774 Constipation Diseases 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000004756 Respiratory Insufficiency Diseases 0.000 description 2
206010038678 Respiratory depression Diseases 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
206010047700 Vomiting Diseases 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000001041 indolyl group Chemical group 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229960005181 morphine Drugs 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229940005483 opioid analgesics Drugs 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
125000003367 polycyclic group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000008673 vomiting Effects 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
GQXASRVHZHNCMW-UHFFFAOYSA-N 7,9-dichloro-4-(4-methoxyphenyl)-2-(5-nitrofuran-2-yl)-3,4-dihydro-2h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1N(C=C(Cl)C=C2Cl)C2=NC(C=2OC(=CC=2)[N+]([O-])=O)C1 GQXASRVHZHNCMW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000005469 ethylenyl group Chemical group 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
150000002306 glutamic acid derivatives Chemical class 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
230000008693 nausea Effects 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
230000002981 neuropathic effect Effects 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000036280 sedation Effects 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed 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
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ZA200303640A 2000-10-13 2003-05-12 Substituted 3.4-dihydro-pyrido[1,2-A]pyrimidines. ZA200303640B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10050662A DE10050662A1 (de)	2000-10-13	2000-10-13	Substituierte 3,4-Dihydro-pyrido[1,2-a]pyrimidine

Publications (1)

Publication Number	Publication Date
ZA200303640B true ZA200303640B (en)	2004-08-12

Family

ID=7659597

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200303640A ZA200303640B (en)	2000-10-13	2003-05-12	Substituted 3.4-dihydro-pyrido[1,2-A]pyrimidines.

Country Status (26)

Country	Link
US (1)	US7230103B2 (fr)
EP (1)	EP1326866B1 (fr)
JP (1)	JP4315678B2 (fr)
KR (1)	KR20030036924A (fr)
CN (1)	CN1255407C (fr)
AR (1)	AR034266A1 (fr)
AT (1)	ATE297927T1 (fr)
AU (2)	AU2002210526B2 (fr)
BR (1)	BR0114734A (fr)
CA (1)	CA2425666A1 (fr)
CO (1)	CO5640115A2 (fr)
DE (2)	DE10050662A1 (fr)
EC (1)	ECSP034553A (fr)
ES (1)	ES2241882T3 (fr)
HU (1)	HUP0302464A2 (fr)
IL (2)	IL155380A0 (fr)
MX (1)	MXPA03003198A (fr)
NO (1)	NO20031412L (fr)
NZ (1)	NZ525652A (fr)
PE (1)	PE20020435A1 (fr)
PL (1)	PL361915A1 (fr)
PT (1)	PT1326866E (fr)
RU (1)	RU2003113966A (fr)
SK (1)	SK4142003A3 (fr)
WO (1)	WO2002030933A1 (fr)
ZA (1)	ZA200303640B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10310106A1 (de) *	2003-03-06	2004-09-16	Grünenthal GmbH	Substituierte Pyridot [1,2-a]pyrimidin-Verbindungen
RU2269538C1 (ru) *	2004-12-30	2006-02-10	Общество с ограниченной ответственностью "Исследовательский Институт Химического Разнообразия" (ООО "Исследовательский Институт Химического Разнообразия")	ЗАМЕЩЕННЫЕ ПИРИДО[4',3':5,6]ПИРАНО[2,3-d]ПИРИМИДИНЫ И КОМБИНАТОРНАЯ БИБЛИОТЕКА
US20070155738A1 (en)	2005-05-20	2007-07-05	Alantos Pharmaceuticals, Inc.	Heterobicyclic metalloprotease inhibitors
JP2012513400A (ja) *	2008-12-22	2012-06-14	シェーリングコーポレイション	γ−セクレターゼ調節剤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178910B (en) *	1977-08-19	1982-07-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing 2,3-disubstituted-4-oxo-4h-pyrido/1,2-a/-pyrimidines
US4666912A (en) *	1984-11-12	1987-05-19	Chinoin Gyogyszer Es Vegyeszeti Termeker Gyara Rt	Treating process

2000
- 2000-10-13 DE DE10050662A patent/DE10050662A1/de not_active Withdrawn
2001
- 2001-10-09 AR ARP010104731A patent/AR034266A1/es unknown
- 2001-10-10 DE DE50106542T patent/DE50106542D1/de not_active Expired - Lifetime
- 2001-10-10 MX MXPA03003198A patent/MXPA03003198A/es active IP Right Grant
- 2001-10-10 JP JP2002534319A patent/JP4315678B2/ja not_active Expired - Fee Related
- 2001-10-10 SK SK414-2003A patent/SK4142003A3/sk not_active Application Discontinuation
- 2001-10-10 EP EP01978402A patent/EP1326866B1/fr not_active Expired - Lifetime
- 2001-10-10 HU HU0302464A patent/HUP0302464A2/hu unknown
- 2001-10-10 AU AU2002210526A patent/AU2002210526B2/en not_active Ceased
- 2001-10-10 PL PL01361915A patent/PL361915A1/xx not_active Application Discontinuation
- 2001-10-10 AT AT01978402T patent/ATE297927T1/de active
- 2001-10-10 CA CA002425666A patent/CA2425666A1/fr not_active Abandoned
- 2001-10-10 RU RU2003113966/04A patent/RU2003113966A/ru not_active Application Discontinuation
- 2001-10-10 KR KR10-2003-7005162A patent/KR20030036924A/ko not_active Withdrawn
- 2001-10-10 AU AU1052602A patent/AU1052602A/xx active Pending
- 2001-10-10 IL IL15538001A patent/IL155380A0/xx active IP Right Grant
- 2001-10-10 PT PT01978402T patent/PT1326866E/pt unknown
- 2001-10-10 CN CNB018205011A patent/CN1255407C/zh not_active Expired - Fee Related
- 2001-10-10 WO PCT/EP2001/011700 patent/WO2002030933A1/fr not_active Ceased
- 2001-10-10 NZ NZ525652A patent/NZ525652A/en unknown
- 2001-10-10 ES ES01978402T patent/ES2241882T3/es not_active Expired - Lifetime
- 2001-10-10 BR BR0114734-0A patent/BR0114734A/pt not_active Application Discontinuation
- 2001-10-12 PE PE2001001014A patent/PE20020435A1/es not_active Application Discontinuation
2003
- 2003-03-27 NO NO20031412A patent/NO20031412L/no not_active Application Discontinuation
- 2003-04-10 IL IL155380A patent/IL155380A/en not_active IP Right Cessation
- 2003-04-11 US US10/411,390 patent/US7230103B2/en not_active Expired - Fee Related
- 2003-04-11 EC EC2003004553A patent/ECSP034553A/es unknown
- 2003-04-11 CO CO03031095A patent/CO5640115A2/es not_active Application Discontinuation
- 2003-05-12 ZA ZA200303640A patent/ZA200303640B/en unknown

Also Published As

Publication number	Publication date
ECSP034553A (es)	2003-05-26
HUP0302464A2 (hu)	2003-11-28
CA2425666A1 (fr)	2003-04-11
JP4315678B2 (ja)	2009-08-19
WO2002030933A1 (fr)	2002-04-18
NO20031412L (no)	2003-04-22
CN1255407C (zh)	2006-05-10
MXPA03003198A (es)	2004-05-21
PL361915A1 (en)	2004-10-04
IL155380A (en)	2009-02-11
SK4142003A3 (en)	2003-10-07
PE20020435A1 (es)	2002-05-18
CO5640115A2 (es)	2006-05-31
JP2004511484A (ja)	2004-04-15
AU1052602A (en)	2002-04-22
US7230103B2 (en)	2007-06-12
ES2241882T3 (es)	2005-11-01
EP1326866A1 (fr)	2003-07-16
KR20030036924A (ko)	2003-05-09
DE10050662A1 (de)	2002-04-18
BR0114734A (pt)	2003-07-01
PT1326866E (pt)	2005-08-31
DE50106542D1 (de)	2005-07-21
NO20031412D0 (no)	2003-03-27
US20030229104A1 (en)	2003-12-11
AU2002210526B2 (en)	2006-10-19
RU2003113966A (ru)	2004-12-10
NZ525652A (en)	2005-01-28
HK1057551A1 (en)	2004-04-08
AR034266A1 (es)	2004-02-18
CN1479740A (zh)	2004-03-03
IL155380A0 (en)	2003-11-23
ATE297927T1 (de)	2005-07-15
EP1326866B1 (fr)	2005-06-15

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ZA200303640B (en)	2004-08-12	Substituted 3.4-dihydro-pyrido[1,2-A]pyrimidines.
JP2007517868A (ja)	2007-07-05	治療薬ｉ
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