SE450573B - 1h-pyrazolo/1,5-a/pyrimidiner, framstellning derav och farmaceutisk komposition - Google Patents

1h-pyrazolo/1,5-a/pyrimidiner, framstellning derav och farmaceutisk komposition

Info

Publication number: SE450573B
Authority: SE; Sweden
Prior art keywords: alkyl; formula; phenyl; compound; pyridyl
Prior art date: 1982-03-16

Application number

SE8301412A

Other languages

English (en)

Swedish (sv)

Other versions

SE8301412D0 (sv

SE8301412L (sv

Inventor

G Doria

C Passarotti

A Buttinoni

Original Assignee

Erba Farmitalia

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.)

1982-03-16

Filing date

1983-03-15

Publication date

1987-07-06

1983-02-04 Priority claimed from GB838303089A external-priority patent/GB8303089D0/en

1983-03-15 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1983-03-15 Publication of SE8301412D0 publication Critical patent/SE8301412D0/xx

1983-09-17 Publication of SE8301412L publication Critical patent/SE8301412L/xx

1987-07-06 Publication of SE450573B publication Critical patent/SE450573B/sv

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 3
150000003230 pyrimidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 126
-1 hydroxy, formyloxy Chemical group 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
239000000460 chlorine Substances 0.000 claims description 27
229910052801 chlorine Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 16
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
230000003110 anti-inflammatory effect Effects 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
UFCYUAUOWBYRLT-UHFFFAOYSA-N 5-methyl-7-oxo-1-phenyl-n-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-6-carboxamide Chemical compound N12C(=O)C(C(=O)NC=3N=CC=CC=3)=C(C)N=C2C=CN1C1=CC=CC=C1 UFCYUAUOWBYRLT-UHFFFAOYSA-N 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
230000000202 analgesic effect Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
230000000269 nucleophilic effect Effects 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
CGNFVIVDXWTWEF-UHFFFAOYSA-N 7-oxo-1-phenyl-n-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-6-carboxamide Chemical compound C=1N=C2C=CN(C=3C=CC=CC=3)N2C(=O)C=1C(=O)NC1=CC=CC=N1 CGNFVIVDXWTWEF-UHFFFAOYSA-N 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
238000000354 decomposition reaction Methods 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 14
238000002425 crystallisation Methods 0.000 description 13
230000008025 crystallization Effects 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229920000137 polyphosphoric acid Polymers 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000243 solution Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
239000005457 ice water Substances 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
238000006386 neutralization reaction Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
235000010418 carrageenan Nutrition 0.000 description 5
239000000679 carrageenan Substances 0.000 description 5
229920001525 carrageenan Polymers 0.000 description 5
229940113118 carrageenan Drugs 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
238000012360 testing method Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
230000007306 turnover Effects 0.000 description 5
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
ZBFTVSVCTKQPTQ-UHFFFAOYSA-N 7-oxo-1-phenylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid Chemical compound N12C(=O)C(C(=O)O)=CN=C2C=CN1C1=CC=CC=C1 ZBFTVSVCTKQPTQ-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 3
PWKUIFKQMLYWNX-UHFFFAOYSA-N 7-oxo-1-phenylpyrazolo[1,5-a]pyrimidine-6-carbonyl chloride Chemical compound N12C(=O)C(C(=O)Cl)=CN=C2C=CN1C1=CC=CC=C1 PWKUIFKQMLYWNX-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
229910019213 POCl3 Inorganic materials 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 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
239000003480 eluent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
210000004197 pelvis Anatomy 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000003883 substance clean up Methods 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 description 2
235000019759 Maize starch Nutrition 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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240000003801 Sigesbeckia orientalis Species 0.000 description 2
235000003407 Sigesbeckia orientalis Nutrition 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
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230000037396 body weight Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ZPJMGOLSPRNUMH-UHFFFAOYSA-N ethyl 1-benzyl-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate Chemical compound C(C)OC(=O)C1=CN=C2N(C1=O)N(C=C2)CC1=CC=CC=C1 ZPJMGOLSPRNUMH-UHFFFAOYSA-N 0.000 description 2
239000008103 glucose Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
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235000005985 organic acids Nutrition 0.000 description 1
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201000008482 osteoarthritis Diseases 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
229940071117 starch glycolate Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SE8301412A 1982-03-16 1983-03-15 1h-pyrazolo/1,5-a/pyrimidiner, framstellning derav och farmaceutisk komposition SE450573B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8207637		1982-03-16
GB838303089A GB8303089D0 (en)	1983-02-04	1983-02-04	Substituted 1h-pyrazolo 1,5-a pyrimidines

Publications (3)

Publication Number	Publication Date
SE8301412D0 SE8301412D0 (sv)	1983-03-15
SE8301412L SE8301412L (sv)	1983-09-17
SE450573B true SE450573B (sv)	1987-07-06

Family

ID=26282260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8301412A SE450573B (sv)	1982-03-16	1983-03-15	1h-pyrazolo/1,5-a/pyrimidiner, framstellning derav och farmaceutisk komposition

Country Status (13)

Country	Link
US (1)	US4482555A (da)
AU (1)	AU557300B2 (da)
CA (1)	CA1192546A (da)
CH (1)	CH654306A5 (da)
DE (1)	DE3309432A1 (da)
DK (1)	DK120783A (da)
FI (1)	FI74469C (da)
FR (1)	FR2523582B1 (da)
IL (1)	IL68133A (da)
IT (1)	IT1194555B (da)
NL (1)	NL8300934A (da)
SE (1)	SE450573B (da)
SU (1)	SU1366060A3 (da)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USD344263S (en)	1991-11-15	1994-02-15	Masami Seido	Plug-receiving metal fitting
RU2147584C1 (ru) *	1995-10-27	2000-04-20	Американ Цианамид Компани	Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов
US6245759B1 (en)	1999-03-11	2001-06-12	Merck & Co., Inc.	Tyrosine kinase inhibitors
MY125533A (en)	1999-12-06	2006-08-30	Bristol Myers Squibb Co	Heterocyclic dihydropyrimidine compounds
EP1782859A3 (en) *	2003-04-11	2009-09-30	High Point Pharmaceuticals, LLC	Pharmaceutical use of substituted pyrazolo [1,5- a]pyrimidines
EP1615697A2 (en) *	2003-04-11	2006-01-18	Novo Nordisk A/S	New pyrazolo[1,5-a] pyrimidine derivatives and pharmaceutical use thereof
US7772232B2 (en)	2004-04-15	2010-08-10	Bristol-Myers Squibb Company	Quinazolinyl compounds as inhibitors of potassium channel function
EP1802623A1 (en) *	2004-10-12	2007-07-04	Novo Nordisk A/S	11beta-hydroxysteroid dehydrogenase type 1 active spiro compounds
WO2007051811A2 (en) *	2005-11-01	2007-05-10	Transtech Pharma	Pharmaceutical use of substituted amides
EA200801243A1 (ru) *	2005-11-01	2008-10-30	Транстек Фарма	Фармацевтическое применение замещенных амидов
EP2007722A1 (en) *	2006-03-21	2008-12-31	High Point Pharmaceuticals, LLC	Adamantane derivatives for the treatment of the metabolic syndrome
EP2010479A1 (en)	2006-04-07	2009-01-07	High Point Pharmaceuticals, LLC	11 beta-hydroxysteroid dehydrogenase type 1 active compounds
WO2007144394A2 (en) *	2006-06-16	2007-12-21	High Point Pharmaceuticals, Llc.	Pharmaceutical use of substituted piperidine carboxamides
US8048908B2 (en) *	2006-07-13	2011-11-01	High Point Pharmaceuticals, Llc	11β-hydroxysteroid dehydrogenase type 1 active compounds
EP1878721A1 (en) *	2006-07-13	2008-01-16	Novo Nordisk A/S	4-Piperidylbenzamides as 11-beta-hydroxysteroid dehydrogenase type 1 inhibitors
US20110003856A1 (en) *	2007-02-23	2011-01-06	Soren Ebdrup	N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase
ZA200904916B (en)	2007-02-23	2010-09-29	High Point Pharmaceuticals Llc	N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase
US8334305B2 (en) *	2007-02-23	2012-12-18	High Point Pharmaceuticals, Llc	N-adamantyl benzamides as inhibitors of 11-β-hydroxysteroid dehydrogenase
EP2146952A1 (en) *	2007-02-23	2010-01-27	High Point Pharmaceuticals, LLC	N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase
US8153798B2 (en) *	2007-03-09	2012-04-10	High Point Pharmaceuticals, Llc	Indole- and benzimidazole amides as hydroxysteroid dehydrogenase inhibitors
CA2681934A1 (en) *	2007-03-28	2008-10-02	High Point Pharmaceuticals, Llc	11beta-hsd1 active compounds
JP2010523692A (ja) *	2007-04-11	2010-07-15	ハイポイントファーマシューティカルズ，リミティドライアビリティカンパニー	新規合成物
ES2393230T3 (es) *	2007-04-24	2012-12-19	High Point Pharmaceuticals, Llc	Uso farmacéutico de amidas sustituidas

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE786611A (fr) *	1971-08-16	1973-01-22	Int Chem & Nuclear Corp	Nouveaux inhibiteurs de xanthine-oxydase et leur procede de preparatio
US3907799A (en) *	1971-08-16	1975-09-23	Icn Pharmaceuticals	Xanthine oxidase inhibitors
US3925385A (en) *	1972-04-20	1975-12-09	Icn Pharmaceuticals	6-Carbethoxy-3,7-disubstitutedpyrazolo{8 1,5a{9 pyrimidines
BE792533A (fr) *	1971-12-09	1973-06-08	Int Chem & Nuclear Corp	Nouvelles pyrazolo (1,5a) pyrimidines et leur procede de preparation
US4093617A (en) *	1974-11-12	1978-06-06	Icn Pharmaceuticals, Inc.	3,5,7-Trisubstituted pyrazolo[1,5-a]pyrimidines
US4048184A (en) *	1976-11-15	1977-09-13	E. R. Squibb & Sons, Inc.	6-Phenyl-2H-pyrazolo[3,4-b]pyridines
US4281000A (en) *	1979-07-09	1981-07-28	American Cyanamid Company	Substituted pyrazolo (1,5-a)pyrimidines and their use as anxiolytic agents

1983
- 1983-03-09 AU AU12304/83A patent/AU557300B2/en not_active Ceased
- 1983-03-10 US US06/474,205 patent/US4482555A/en not_active Expired - Fee Related
- 1983-03-11 CH CH1325/83A patent/CH654306A5/de not_active IP Right Cessation
- 1983-03-11 IT IT20024/83A patent/IT1194555B/it active
- 1983-03-15 IL IL68133A patent/IL68133A/xx unknown
- 1983-03-15 DK DK120783A patent/DK120783A/da not_active Application Discontinuation
- 1983-03-15 SU SU833565748A patent/SU1366060A3/ru active
- 1983-03-15 SE SE8301412A patent/SE450573B/sv not_active IP Right Cessation
- 1983-03-15 CA CA000423644A patent/CA1192546A/en not_active Expired
- 1983-03-15 FR FR8304253A patent/FR2523582B1/fr not_active Expired
- 1983-03-15 FI FI830864A patent/FI74469C/fi not_active IP Right Cessation
- 1983-03-15 NL NL8300934A patent/NL8300934A/xx active Search and Examination
- 1983-03-16 DE DE19833309432 patent/DE3309432A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
CA1192546A (en)	1985-08-27
SU1366060A3 (ru)	1988-01-07
IT8320024A0 (it)	1983-03-11
FI830864L (fi)	1983-09-17
SE8301412D0 (sv)	1983-03-15
AU1230483A (en)	1983-09-22
IL68133A0 (en)	1983-06-15
FI74469C (fi)	1988-02-08
FR2523582A1 (fr)	1983-09-23
DE3309432A1 (de)	1983-09-22
NL8300934A (nl)	1983-10-17
IL68133A (en)	1985-12-31
DK120783A (da)	1983-09-17
DK120783D0 (da)	1983-03-15
FR2523582B1 (fr)	1985-12-06
IT1194555B (it)	1988-09-22
AU557300B2 (en)	1986-12-18
US4482555A (en)	1984-11-13
SE8301412L (sv)	1983-09-17
FI830864A0 (fi)	1983-03-15
FI74469B (fi)	1987-10-30
CH654306A5 (de)	1986-02-14

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