DD293823A5 - Verfahren zur herstellung von triazolopyridinen - Google Patents

Verfahren zur herstellung von triazolopyridinen Download PDF

Info

Publication number: DD293823A5
Authority: DD; German Democratic Republic
Prior art keywords: pyridine; amino; compound; preparation; difluoro
Prior art date: 1989-04-21

Application number

DD90339946A

Other languages

German (de)

English (en)

Inventor

James L Kelley

Original Assignee

��@��@��@��k��

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.)

1989-04-21

Filing date

1990-04-20

Publication date

1991-09-12

1990-04-20 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1991-09-12 Publication of DD293823A5 publication Critical patent/DD293823A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 31
238000000034 method Methods 0.000 title claims abstract description 21
150000008523 triazolopyridines Chemical class 0.000 title claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 49
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
-1 2,5-difluorobenzyl Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims 1
125000005110 aryl thio group Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 48
206010015037 epilepsy Diseases 0.000 abstract description 10
241000124008 Mammalia Species 0.000 abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
239000008194 pharmaceutical composition Chemical class 0.000 abstract description 3
YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 24
239000007787 solid Substances 0.000 description 23
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
239000000872 buffer Substances 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
239000012458 free base Substances 0.000 description 10
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000725 suspension Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 description 7
239000001961 anticonvulsive agent Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000003755 preservative agent Substances 0.000 description 6
LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 description 5
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 5
229960003965 antiepileptics Drugs 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000008213 purified water Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
PQCUDKMMPTXMAL-UHFFFAOYSA-N (2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1F PQCUDKMMPTXMAL-UHFFFAOYSA-N 0.000 description 4
DNMSCFKODPUARU-UHFFFAOYSA-N 2-chloro-4-n-[(2-fluorophenyl)methyl]pyridine-3,4-diamine Chemical compound NC1=C(Cl)N=CC=C1NCC1=CC=CC=C1F DNMSCFKODPUARU-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
230000001773 anti-convulsant effect Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
229940099112 cornstarch Drugs 0.000 description 4
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
ZPPGXLNSBMRJQE-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-3-nitropyridin-4-amine Chemical compound [O-][N+](=O)C1=CN=CC=C1NCC1=C(F)C=CC=C1F ZPPGXLNSBMRJQE-UHFFFAOYSA-N 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
230000002335 preservative effect Effects 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
239000008117 stearic acid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
ZAXYOUDKPOIFEH-UHFFFAOYSA-N 2-chloro-4-n-[(2,6-difluorophenyl)methyl]pyridine-3,4-diamine Chemical compound NC1=C(Cl)N=CC=C1NCC1=C(F)C=CC=C1F ZAXYOUDKPOIFEH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
208000015114 central nervous system disease Diseases 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
239000003814 drug Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
SERWGCSOYHJNQW-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-methyltriazolo[4,5-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=NC=2C(NC)=NC=CC=2N1CC1=CC=CC=C1F SERWGCSOYHJNQW-UHFFFAOYSA-N 0.000 description 2
QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 2
ABOSMHRLVUWEMT-UHFFFAOYSA-N 4-ethoxy-3-nitropyridine Chemical compound CCOC1=CC=NC=C1[N+]([O-])=O ABOSMHRLVUWEMT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical group NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 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
241000282412 Homo Species 0.000 description 2
241001465754 Metazoa Species 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
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000036461 convulsion Effects 0.000 description 2
125000006317 cyclopropyl amino group Chemical group 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-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
239000007788 liquid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
ARIKIVYNWXFQEJ-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-3-nitropyridin-4-amine Chemical compound [O-][N+](=O)C1=CN=CC=C1NCC1=CC=CC=C1F ARIKIVYNWXFQEJ-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GDFBHCMFIUBEQT-UHFFFAOYSA-N (2,5-difluorophenyl)methanamine Chemical group NCC1=CC(F)=CC=C1F GDFBHCMFIUBEQT-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RHPNQQDWURLQKE-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-n-methyltriazolo[4,5-c]pyridin-4-amine Chemical compound N1=NC=2C(NC)=NC=CC=2N1CC1=C(F)C=CC=C1F RHPNQQDWURLQKE-UHFFFAOYSA-N 0.000 description 1
YALSADUGEMVJKF-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-methyltriazolo[4,5-c]pyridin-4-amine Chemical compound N1=NC=2C(NC)=NC=CC=2N1CC1=CC=CC=C1F YALSADUGEMVJKF-UHFFFAOYSA-N 0.000 description 1
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
RLYSLNURZIHNIW-UHFFFAOYSA-N 2-chloro-4-n-[(2,5-difluorophenyl)methyl]pyridine-3,4-diamine Chemical compound NC1=C(Cl)N=CC=C1NCC1=CC(F)=CC=C1F RLYSLNURZIHNIW-UHFFFAOYSA-N 0.000 description 1
GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
JAEDREONBIBHBV-UHFFFAOYSA-N 4-[(2-fluorophenyl)methyl]-3-nitropyridin-2-amine Chemical group FC1=C(CC2=C(C(=NC=C2)N)[N+](=O)[O-])C=CC=C1 JAEDREONBIBHBV-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
GVUIJRYHZUTCKN-UHFFFAOYSA-N 4-chloro-1-[(2,6-difluorophenyl)methyl]triazolo[4,5-c]pyridine Chemical compound FC1=CC=CC(F)=C1CN1C2=CC=NC(Cl)=C2N=N1 GVUIJRYHZUTCKN-UHFFFAOYSA-N 0.000 description 1
JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 description 1
HNMWMLXQJBWURC-UHFFFAOYSA-N 4-ethoxy-3-nitropyridin-1-ium;chloride Chemical compound Cl.CCOC1=CC=NC=C1[N+]([O-])=O HNMWMLXQJBWURC-UHFFFAOYSA-N 0.000 description 1
KIUJRSWVKVXUDT-UHFFFAOYSA-N 4-n-benzyl-2-chloropyridine-3,4-diamine Chemical compound NC1=C(Cl)N=CC=C1NCC1=CC=CC=C1 KIUJRSWVKVXUDT-UHFFFAOYSA-N 0.000 description 1
OSBNEKYMSBKRRI-UHFFFAOYSA-N 9-[fluoro(phenyl)methyl]purin-6-amine Chemical class C1=NC=2C(N)=NC=NC=2N1C(F)C1=CC=CC=C1 OSBNEKYMSBKRRI-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000017667 Chronic Disease Diseases 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
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
206010017711 Gangrene Diseases 0.000 description 1
208000034308 Grand mal convulsion Diseases 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
239000004909 Moisturizer Substances 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 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
229920001615 Tragacanth Polymers 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004659 aryl alkyl thio group Chemical group 0.000 description 1
239000000305 astragalus gummifer gum Substances 0.000 description 1
230000002567 autonomic effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
210000004556 brain Anatomy 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
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000011928 denatured alcohol Substances 0.000 description 1
125000006287 difluorobenzyl group Chemical group 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000002895 emetic Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229940060367 inert ingredients Drugs 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229940045996 isethionic acid Drugs 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229940099563 lactobionic acid Drugs 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000001333 moisturizer Effects 0.000 description 1
QKGLPYAAPIWCKO-UHFFFAOYSA-N n-[(2,5-difluorophenyl)methyl]-3-nitropyridin-4-amine Chemical compound [O-][N+](=O)C1=CN=CC=C1NCC1=CC(F)=CC=C1F QKGLPYAAPIWCKO-UHFFFAOYSA-N 0.000 description 1
MEVVLVNFFGTNKY-UHFFFAOYSA-N n-benzyl-3-nitropyridin-4-amine Chemical compound [O-][N+](=O)C1=CN=CC=C1NCC1=CC=CC=C1 MEVVLVNFFGTNKY-UHFFFAOYSA-N 0.000 description 1
GIMLSWPGAVXCCQ-UHFFFAOYSA-N n-cyclopropyl-1-[(2,6-difluorophenyl)methyl]triazolo[4,5-c]pyridin-4-amine Chemical compound FC1=CC=CC(F)=C1CN1C2=CC=NC(NC3CC3)=C2N=N1 GIMLSWPGAVXCCQ-UHFFFAOYSA-N 0.000 description 1
230000008693 nausea Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960002036 phenytoin Drugs 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
230000035939 shock Effects 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
239000007901 soft capsule Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A61P25/08—Antiepileptics; Anticonvulsants

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Biomedical Technology (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)
Neurology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD90339946A 1989-04-21 1990-04-20 Verfahren zur herstellung von triazolopyridinen DD293823A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898909136A GB8909136D0 (en)	1989-04-21	1989-04-21	Anticonvulsant pyridines and analogues thereof

Publications (1)

Publication Number	Publication Date
DD293823A5 true DD293823A5 (de)	1991-09-12

Family

ID=10655494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90339946A DD293823A5 (de)	1989-04-21	1990-04-20	Verfahren zur herstellung von triazolopyridinen

Country Status (21)

Country	Link
EP (1)	EP0399653B1 (da)
JP (1)	JP2865367B2 (da)
KR (1)	KR0183972B1 (da)
AT (1)	ATE113046T1 (da)
CA (1)	CA2015047A1 (da)
CY (1)	CY2003B1 (da)
DD (1)	DD293823A5 (da)
DE (1)	DE69013396T2 (da)
DK (1)	DK0399653T3 (da)
ES (1)	ES2062351T3 (da)
FI (1)	FI93448C (da)
GB (1)	GB8909136D0 (da)
HK (1)	HK78397A (da)
HU (2)	HU206210B (da)
IE (1)	IE67335B1 (da)
IL (1)	IL94150A (da)
LV (1)	LV5780B4 (da)
NZ (1)	NZ233404A (da)
PH (1)	PH27118A (da)
PT (1)	PT93822B (da)
ZA (1)	ZA903021B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1087968A1 (en) *	1998-06-16	2001-04-04	MERCK SHARP & DOHME LTD.	Triazolo-pyridine derivatives as ligands for gaba receptors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3929812A (en) *	1974-05-20	1975-12-30	Squibb & Sons Inc	Derivatives of 1H-triazolo {8 4,5-c{9 pyridine-7-carboxylic acids and esters
DE3873812D1 (de) *	1987-04-07	1992-09-24	Ciba Geigy Ag	3h-1,2,3-triazolo(4,5-d)pyrimidine.

1989
- 1989-04-21 GB GB898909136A patent/GB8909136D0/en active Pending
1990
- 1990-04-19 PH PH40399A patent/PH27118A/en unknown
- 1990-04-20 PT PT93822A patent/PT93822B/pt not_active IP Right Cessation
- 1990-04-20 EP EP90304271A patent/EP0399653B1/en not_active Expired - Lifetime
- 1990-04-20 DK DK90304271.1T patent/DK0399653T3/da active
- 1990-04-20 FI FI901981A patent/FI93448C/fi not_active IP Right Cessation
- 1990-04-20 CA CA002015047A patent/CA2015047A1/en not_active Abandoned
- 1990-04-20 IE IE140990A patent/IE67335B1/en not_active IP Right Cessation
- 1990-04-20 KR KR1019900005523A patent/KR0183972B1/ko not_active Expired - Fee Related
- 1990-04-20 ZA ZA903021A patent/ZA903021B/xx unknown
- 1990-04-20 AT AT90304271T patent/ATE113046T1/de not_active IP Right Cessation
- 1990-04-20 HU HU902502A patent/HU206210B/hu not_active IP Right Cessation
- 1990-04-20 JP JP2105156A patent/JP2865367B2/ja not_active Expired - Lifetime
- 1990-04-20 ES ES90304271T patent/ES2062351T3/es not_active Expired - Lifetime
- 1990-04-20 IL IL9415090A patent/IL94150A/en not_active IP Right Cessation
- 1990-04-20 DD DD90339946A patent/DD293823A5/de not_active IP Right Cessation
- 1990-04-20 NZ NZ233404A patent/NZ233404A/en unknown
- 1990-04-20 DE DE69013396T patent/DE69013396T2/de not_active Expired - Fee Related
1995
- 1995-05-11 HU HU95P/P00126P patent/HU211137A9/hu unknown
1996
- 1996-07-17 LV LV960252A patent/LV5780B4/xx unknown
1997
- 1997-06-12 HK HK78397A patent/HK78397A/en not_active IP Right Cessation
1998
- 1998-04-30 CY CY9802003A patent/CY2003B1/xx unknown

Also Published As

Publication number	Publication date
IL94150A (en)	1994-02-27
IE67335B1 (en)	1996-03-20
HU206210B (en)	1992-09-28
NZ233404A (en)	1992-08-26
JP2865367B2 (ja)	1999-03-08
KR0183972B1 (ko)	1999-05-01
AU5372290A (en)	1990-10-25
HU902502D0 (en)	1990-08-28
ATE113046T1 (de)	1994-11-15
EP0399653A1 (en)	1990-11-28
FI93448B (fi)	1994-12-30
DK0399653T3 (da)	1994-11-14
PT93822B (pt)	1996-09-30
HU211137A9 (en)	1995-10-30
LV5780B4 (lv)	1997-04-20
ZA903021B (en)	1991-12-24
LV5780A4 (lv)	1996-12-20
AU626409B2 (en)	1992-07-30
DE69013396D1 (de)	1994-11-24
EP0399653B1 (en)	1994-10-19
GB8909136D0 (en)	1989-06-07
PT93822A (pt)	1990-11-20
FI93448C (fi)	1995-04-10
JPH02292286A (ja)	1990-12-03
DE69013396T2 (de)	1995-05-04
HK78397A (en)	1997-06-20
CY2003B1 (en)	1998-04-30
IE901409L (en)	1990-10-21
ES2062351T3 (es)	1994-12-16
KR900016208A (ko)	1990-11-12
PH27118A (en)	1993-03-16
FI901981A0 (fi)	1990-04-20
CA2015047A1 (en)	1990-10-21
IL94150A0 (en)	1991-01-31
HUT53905A (en)	1990-12-28

Legal Events

Date	Code	Title	Description
1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69804273T2 (de)	2002-10-31	5h-Thiazolo[3,2-a]pyrimidinderivate
DE69926665T2 (de)	2006-06-08	Azolo-Pyrimidine
DE69823648T2 (de)	2005-04-28	1-phenyl-4-benzylpiperazine: spezifische liganden für den dopamin rezeptor (d4)
DE602004005960T2 (de)	2008-01-17	Heteroaryl-substituierte pyrrolä2, 3- büpyridin-derivate als crf-rezeptor-antagonisten
DD291560A5 (de)	1991-07-04	Verfahren zum herstellen von racemischen oder optisch aktiven pyrido [1,2-a] pyrazin-derivaten
EP0063381A1 (de)	1982-10-27	Neue Pyrazolo(3,4-d)pyrimidine, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel
DD207716A5 (de)	1984-03-14	Verfahren zur herstellung von 1,2,4-triazinen und von pyrazinen
DE4430639A1 (de)	1996-03-07	Verwendung von 5-substituierten Pyridin- und Hexahydrochinolin-3-carbonsäurederivaten
DE69925462T2 (de)	2006-02-02	Substituierte cycloalkyl-4-oxonicotinische karboxamide; gaba gehirn-rezeptorligande
DE69031337T2 (de)	1998-03-05	9-substituierte-8-unsubstituierte-9-deazaguanine
DE69916627T2 (de)	2005-07-28	5-heterozyklyl-pyrazolo[4,3-d]pyrimidin-7-one für die behandlung von männlichen erectilen dysfunktionen
WO1992014465A1 (de)	1992-09-03	Verwendung von anellierten tetrahydropyridinessigsäurederivaten für die behandlung neurologischer erkrankungen
EP1296986A1 (de)	2003-04-02	5-aminoalkyl-pyrazolo[4,3-d]pyrimidine mit phosphodiesterase v inhibierender wirkung
DE60026883T2 (de)	2006-11-23	Methoden und zusammensetzungen zur behandlung von schmerzen
DE3439450A1 (de)	1986-05-07	1,2,4-triazolo-carbamate und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel
DE68916198T2 (de)	1994-09-22	Carbamoyl-2-Pyrrolidinonverbindungen.
DE68902490T2 (de)	1992-12-24	Pharmazeutische zusammensetzung.
US5240937A (en)	1993-08-31	Pharmaceutically active triazolopyridine compounds
DE69130266T2 (de)	1999-03-18	Optisch wirksame Alkylendioxybenzolderivate und ihre Verwendung als Arzneimittel
DE69028147T2 (de)	1997-01-02	Antikonvulsive Pirazine
DE69413112T2 (de)	1999-05-12	5-HT3 Pyrrolopyrazinderivate
DD293823A5 (de)	1991-09-12	Verfahren zur herstellung von triazolopyridinen
DE2229845B2 (de)	1980-01-10	6-o-Halogenphenyl-4H-s-triazolo [3,4-c] thieno [2,3e] [1,4] diazepine, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Massen
EP0496274A1 (de)	1992-07-29	Tricyclisches Pyridonderivat
DE4019080A1 (de)	1991-12-19	Neue 3,7-diazabicycolo (3,3,1)nonan-verbindungen enthaltende arzneimittel