IL110622A - Bicyclic carboxamides n-substituted by bridged bicyclic amines - Google Patents

Bicyclic carboxamides n-substituted by bridged bicyclic amines

Info

Publication number: IL110622A
Authority: IL; Israel
Prior art keywords: amino; alkyl; formula; azabicyclo; compounds
Prior art date: 1989-11-28

Application number

IL11062290A

Other languages

English (en)

Original Assignee

Syntex Inc

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.)

1989-11-28

Filing date

1990-11-27

Publication date

1995-03-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23755479&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL110622(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-11-27 Application filed by Syntex Inc filed Critical Syntex Inc

1995-03-30 Publication of IL110622A publication Critical patent/IL110622A/en

Links

-1 Bicyclic carboxamides Chemical class 0.000 title claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 63
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
125000001589 carboacyl group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 12
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 6
125000004423 acyloxy group Chemical group 0.000 claims description 2
238000001727 in vivo Methods 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
229940113081 5 Hydroxytryptamine 3 receptor antagonist Drugs 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 abstract description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 24
238000000034 method Methods 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 18
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 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
150000001412 amines Chemical class 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 6
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 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000010410 layer Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
REUAXQZIRFXQML-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2C(N)CN1CC2 REUAXQZIRFXQML-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
DBPHZCRAKOJSMX-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-amine Chemical compound C1CN2CCC1(N)CC2 DBPHZCRAKOJSMX-UHFFFAOYSA-N 0.000 description 3
GCFQXKYHWFWGSB-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-1-carboxylic acid Chemical compound C1CCCC2=C1C=CC=C2C(=O)O GCFQXKYHWFWGSB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
NWUBOFMDMPMARL-UHFFFAOYSA-N ethyl 2,3-dihydro-1h-indene-4-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1CCC2 NWUBOFMDMPMARL-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
REUAXQZIRFXQML-SSDOTTSWSA-N (3s)-1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2[C@H](N)CN1CC2 REUAXQZIRFXQML-SSDOTTSWSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000010640 amide synthesis reaction Methods 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007790 solid phase Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
REUAXQZIRFXQML-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2[C@@H](N)CN1CC2 REUAXQZIRFXQML-ZETCQYMHSA-N 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
HXZZHYZJJLFSKL-UHFFFAOYSA-N 2,3-dihydro-1h-indene-4-carboxamide Chemical class NC(=O)C1=CC=CC2=C1CCC2 HXZZHYZJJLFSKL-UHFFFAOYSA-N 0.000 description 1
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
XCCRLEOPTMKRRF-UHFFFAOYSA-N 2-methoxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid Chemical group C1CCCC2=C(C(O)=O)C(OC)=CC=C21 XCCRLEOPTMKRRF-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
102000035037 5-HT3 receptors Human genes 0.000 description 1
108091005477 5-HT3 receptors Proteins 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 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
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
206010047700 Vomiting Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002983 circular dichroism Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
KFDMIEKCYNUIEX-UHFFFAOYSA-N ethyl 5-methoxy-2,3-dihydro-1h-indene-4-carboxylate Chemical group C1=C(OC)C(C(=O)OCC)=C2CCCC2=C1 KFDMIEKCYNUIEX-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
HZRMTWQRDMYLNW-UHFFFAOYSA-N lithium metaborate Chemical compound [Li+].[O-]B=O HZRMTWQRDMYLNW-UHFFFAOYSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
KEUCVAJJEJIMHH-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-2,3-dihydro-1h-indene-4-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C1=CC=CC2=C1CCC2 KEUCVAJJEJIMHH-UHFFFAOYSA-N 0.000 description 1
WYTLHFSTKPVHSD-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-methoxy-2,3-dihydro-1h-indene-1-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C1C2=CC=C(OC)C=C2CC1 WYTLHFSTKPVHSD-UHFFFAOYSA-N 0.000 description 1
WIQBEGFSWHRUHQ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-4-yl)-2,3-dihydro-1h-indene-4-carboxamide Chemical compound C1CN(CC2)CCC12NC(=O)C1=CC=CC2=C1CCC2 WIQBEGFSWHRUHQ-UHFFFAOYSA-N 0.000 description 1
KEUCVAJJEJIMHH-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydro-1h-indene-4-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C1=CC=CC2=C1CCC2 KEUCVAJJEJIMHH-MRXNPFEDSA-N 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
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
WVTKBKWTSCPRNU-UHFFFAOYSA-N rac-Tetrandrin Natural products O1C(C(=CC=2CCN3C)OC)=CC=2C3CC(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2CC2N(C)CCC3=CC(OC)=C(OC)C1=C23 WVTKBKWTSCPRNU-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
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- 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
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- 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
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IL11062290A 1989-11-28 1990-11-27 Bicyclic carboxamides n-substituted by bridged bicyclic amines IL110622A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US44208289A	1989-11-28	1989-11-28
IL9648690A IL96486A (en)	1989-11-28	1990-11-27	Tricyclic compounds, their preparation and pharmaceutical compositions containing them

Publications (1)

Publication Number	Publication Date
IL110622A true IL110622A (en)	1995-03-30

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ID=23755479

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Application Number	Title	Priority Date	Filing Date
IL9648690A IL96486A (en)	1989-11-28	1990-11-27	Tricyclic compounds, their preparation and pharmaceutical compositions containing them
IL11062290A IL110622A (en)	1989-11-28	1990-11-27	Bicyclic carboxamides n-substituted by bridged bicyclic amines

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
IL9648690A IL96486A (en)	1989-11-28	1990-11-27	Tricyclic compounds, their preparation and pharmaceutical compositions containing them

Country Status (23)

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US (1)	US5202333A (no)
EP (1)	EP0430190B1 (no)
JP (1)	JPH0662607B2 (no)
KR (1)	KR970007917B1 (no)
AT (1)	ATE124698T1 (no)
AU (1)	AU642178B2 (no)
BR (1)	BR1100680A (no)
CA (1)	CA2030718C (no)
DE (2)	DE69020694T2 (no)
DK (1)	DK0430190T3 (no)
ES (1)	ES2075121T3 (no)
FI (1)	FI98367C (no)
HK (1)	HK36097A (no)
HU (1)	HU218654B (no)
IE (1)	IE68434B1 (no)
IL (2)	IL96486A (no)
LU (1)	LU91162I2 (no)
NL (1)	NL300194I1 (no)
NO (2)	NO175309C (no)
NZ (1)	NZ236225A (no)
PL (3)	PL166267B1 (no)
PT (1)	PT96001B (no)
ZA (1)	ZA909529B (no)

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EP0315390B1 (en) *	1987-11-04	1994-07-20	Beecham Group Plc	Novel 4-oxobenzotriazines and 4-oxoquinazolines
PL166267B1 (pl) *	1989-11-28	1995-04-28	Syntex Inc	Sposób wytwarzania nowych zwiazków trójpierscieniowych PL PL PL PL
AU7618991A (en) *	1990-05-14	1991-11-14	Syntex (U.S.A.) Inc.	Novel tricyclic compounds
US5189041A (en) *	1990-11-16	1993-02-23	Syntex (U.S.A.) Inc.	Tricyclic 5-ht3 receptor antagonists

1990
- 1990-11-27 PL PL90303660A patent/PL166267B1/pl unknown
- 1990-11-27 DK DK90122689.4T patent/DK0430190T3/da active
- 1990-11-27 IE IE426990A patent/IE68434B1/en not_active IP Right Cessation
- 1990-11-27 AU AU66963/90A patent/AU642178B2/en not_active Expired
- 1990-11-27 ZA ZA909529A patent/ZA909529B/xx unknown
- 1990-11-27 EP EP90122689A patent/EP0430190B1/en not_active Expired - Lifetime
- 1990-11-27 NZ NZ236225A patent/NZ236225A/en unknown
- 1990-11-27 FI FI905839A patent/FI98367C/fi active Protection Beyond IP Right Term
- 1990-11-27 DE DE69020694T patent/DE69020694T2/de not_active Expired - Lifetime
- 1990-11-27 PL PL90303661A patent/PL166277B1/pl unknown
- 1990-11-27 HU HU670/90A patent/HU218654B/hu active Protection Beyond IP Right Term
- 1990-11-27 IL IL9648690A patent/IL96486A/en active Protection Beyond IP Right Term
- 1990-11-27 AT AT90122689T patent/ATE124698T1/de active
- 1990-11-27 PT PT96001A patent/PT96001B/pt not_active IP Right Cessation
- 1990-11-27 CA CA002030718A patent/CA2030718C/en not_active Expired - Lifetime
- 1990-11-27 JP JP2328764A patent/JPH0662607B2/ja not_active Expired - Fee Related
- 1990-11-27 NO NO905120A patent/NO175309C/no not_active IP Right Cessation
- 1990-11-27 PL PL90287961A patent/PL166272B1/pl unknown
- 1990-11-27 KR KR1019900019275A patent/KR970007917B1/ko not_active Expired - Lifetime
- 1990-11-27 DE DE200512000027 patent/DE122005000027I2/de active Active
- 1990-11-27 IL IL11062290A patent/IL110622A/en not_active IP Right Cessation
- 1990-11-27 ES ES90122689T patent/ES2075121T3/es not_active Expired - Lifetime
1991
- 1991-05-22 US US07/704,565 patent/US5202333A/en not_active Expired - Lifetime
1997
- 1997-03-20 HK HK36097A patent/HK36097A/en not_active IP Right Cessation
- 1997-05-08 BR BR1100680-3A patent/BR1100680A/pt active IP Right Grant
2005
- 2005-04-18 LU LU91162C patent/LU91162I2/fr unknown
- 2005-04-20 NL NL300194C patent/NL300194I1/nl unknown
- 2005-09-21 NO NO2005023C patent/NO2005023I2/no unknown

Also Published As

Publication number	Publication date
NO2005023I2 (no)	2009-10-05
AU642178B2 (en)	1993-10-14
EP0430190A3 (en)	1992-01-22
EP0430190B1 (en)	1995-07-05
NL300194I2 (nl)	2005-07-01
FI905839L (fi)	1991-05-29
FI905839A0 (fi)	1990-11-27
HU907660D0 (en)	1991-06-28
HK36097A (en)	1997-03-27
PL166267B1 (pl)	1995-04-28
NO2005023I1 (no)	2005-10-03
EP0430190A2 (en)	1991-06-05
IE904269A1 (en)	1991-06-05
NO175309C (no)	1994-09-28
US5202333A (en)	1993-04-13
IL96486A0 (en)	1991-08-16
NO905120L (no)	1991-05-29
IE68434B1 (en)	1996-06-12
ZA909529B (en)	1992-08-26
DE122005000027I1 (de)	2005-08-04
PT96001A (pt)	1991-09-30
FI98367B (fi)	1997-02-28
BR1100680A (pt)	2000-02-08
HU218654B (hu)	2000-10-28
PL166277B1 (pl)	1995-04-28
LU91162I2 (fr)	2005-06-20
CA2030718C (en)	1998-05-12
NO175309B (no)	1994-06-20
DK0430190T3 (da)	1995-08-21
ATE124698T1 (de)	1995-07-15
PL166272B1 (pl)	1995-04-28
FI98367C (fi)	1997-06-10
PT96001B (pt)	1998-01-30
DE122005000027I2 (de)	2006-03-16
DE69020694T2 (de)	1996-01-18
IL96486A (en)	1995-03-30
NO905120D0 (no)	1990-11-27
JPH0662607B2 (ja)	1994-08-17
ES2075121T3 (es)	1995-10-01
KR910009699A (ko)	1991-06-28
HUT56368A (en)	1991-08-28
NZ236225A (en)	1992-09-25
KR970007917B1 (ko)	1997-05-17
JPH03176486A (ja)	1991-07-31
AU6696390A (en)	1991-06-06
CA2030718A1 (en)	1991-05-29
DE69020694D1 (de)	1995-08-10
PL287961A1 (en)	1991-12-02
NL300194I1 (nl)	2005-07-01

Legal Events

Date	Code	Title
1997-02-18	KB	Patent renewed
2001-04-30	KB	Patent renewed
2005-02-20	KB	Patent renewed
2009-06-15	KB	Patent renewed
2011-07-31	EXP	Patent expired

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CA2042443A1 (en)	1991-11-15	Tricyclic compounds
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EP2155199A2 (en)	2010-02-24	Novel palonosetron salts and processes for preparation and purification thereof
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