DE2458176A1 - Substituierte 1,3-dihydrospiro eckige klammer auf isobenzofurane eckige klammer zu - Google Patents
Substituierte 1,3-dihydrospiro eckige klammer auf isobenzofurane eckige klammer zuInfo
- Publication number
- DE2458176A1 DE2458176A1 DE19742458176 DE2458176A DE2458176A1 DE 2458176 A1 DE2458176 A1 DE 2458176A1 DE 19742458176 DE19742458176 DE 19742458176 DE 2458176 A DE2458176 A DE 2458176A DE 2458176 A1 DE2458176 A1 DE 2458176A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- isobenzofuran
- group
- dihydrospiro
- hydroxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 69
- -1 methylenedioxy group Chemical group 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000003003 spiro group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000004795 grignard reagents Chemical class 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 150000002641 lithium Chemical class 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 150000003891 oxalate salts Chemical class 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 241000251730 Chondrichthyes Species 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000003936 benzamides Chemical class 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical class C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002918 oxazolines Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 239000013078 crystal Substances 0.000 description 38
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 3
- XLCYXINIUJNTPF-UHFFFAOYSA-N 2-(2-bromophenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C(=CC=CC=2)Br)=N1 XLCYXINIUJNTPF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- IOWGHQGLUMEZKG-UHFFFAOYSA-N (2-bromophenyl)methanol Chemical compound OCC1=CC=CC=C1Br IOWGHQGLUMEZKG-UHFFFAOYSA-N 0.000 description 2
- OHNMYFOLDDPTQR-UHFFFAOYSA-N 1-benzyl-3-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]piperidin-3-ol Chemical compound CC1(C)COC(C=2C(=CC=CC=2)C2(O)CN(CC=3C=CC=CC=3)CCC2)=N1 OHNMYFOLDDPTQR-UHFFFAOYSA-N 0.000 description 2
- MQISNDAUWVHJML-UHFFFAOYSA-N 1-butyl-4-fluorobenzene Chemical compound CCCCC1=CC=C(F)C=C1 MQISNDAUWVHJML-UHFFFAOYSA-N 0.000 description 2
- ILZYXPIIYMNWEE-UHFFFAOYSA-N 2-(2-bromo-4,5-dimethoxyphenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C1=NC(C)(C)CO1 ILZYXPIIYMNWEE-UHFFFAOYSA-N 0.000 description 2
- MKLPVCPLEZZAQM-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound COC1=CC=C(Br)C(C=2OCC(C)(C)N=2)=C1 MKLPVCPLEZZAQM-UHFFFAOYSA-N 0.000 description 2
- QUZXRGPANCATEX-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C(=CC(F)=CC=2)Cl)=N1 QUZXRGPANCATEX-UHFFFAOYSA-N 0.000 description 2
- SKXKZDUTELKKAV-UHFFFAOYSA-N 2-(6-bromo-1,3-benzodioxol-5-yl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C(=CC=3OCOC=3C=2)Br)=N1 SKXKZDUTELKKAV-UHFFFAOYSA-N 0.000 description 2
- 125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 description 2
- YXLYUMKNPBVOKB-UHFFFAOYSA-N 2-bromo-n-(1-hydroxy-2-methylpropan-2-yl)-5-methoxybenzamide Chemical compound COC1=CC=C(Br)C(C(=O)NC(C)(C)CO)=C1 YXLYUMKNPBVOKB-UHFFFAOYSA-N 0.000 description 2
- LMFNTOPITQZOCK-UHFFFAOYSA-N 2-chloro-4-fluoro-n-(1-hydroxy-2-methylpropan-2-yl)benzamide Chemical compound OCC(C)(C)NC(=O)C1=CC=C(F)C=C1Cl LMFNTOPITQZOCK-UHFFFAOYSA-N 0.000 description 2
- ICMJMKOIRYHDBC-UHFFFAOYSA-N 4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC=CC=C1C1=NC(C)(C)CO1 ICMJMKOIRYHDBC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000124008 Mammalia Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- BYOIMOJOKVUNTP-UHFFFAOYSA-N spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C12=CC=CC=C2COC21CCNCC2 BYOIMOJOKVUNTP-UHFFFAOYSA-N 0.000 description 2
- RNMPNVBLQHYANU-UHFFFAOYSA-N spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC21CCNCC2 RNMPNVBLQHYANU-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- HXGZPMHPSBJMKB-UHFFFAOYSA-N (2-bromo-5-fluorophenyl)methanol Chemical compound OCC1=CC(F)=CC=C1Br HXGZPMHPSBJMKB-UHFFFAOYSA-N 0.000 description 1
- JQZMYHGPOGEZMA-UHFFFAOYSA-N 1'-[4,4-bis(4-fluorophenyl)butyl]spiro[1h-2-benzofuran-3,4'-piperidine];hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C3=CC=CC=C3CO2)CC1 JQZMYHGPOGEZMA-UHFFFAOYSA-N 0.000 description 1
- ILOMMMNNLDJQCU-UHFFFAOYSA-N 1'-acetylspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1CN(C(=O)C)CCC21C1=CC=CC=C1C(=O)O2 ILOMMMNNLDJQCU-UHFFFAOYSA-N 0.000 description 1
- QOWYAZGBNNEQOA-UHFFFAOYSA-N 1'-benzyl-5,6-dimethoxyspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(=O)OC1(CC1)CCN1CC1=CC=CC=C1 QOWYAZGBNNEQOA-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- ZRSGZIMDIHBXIN-UHFFFAOYSA-N 1,3-benzodioxole-5-carbonyl chloride Chemical compound ClC(=O)C1=CC=C2OCOC2=C1 ZRSGZIMDIHBXIN-UHFFFAOYSA-N 0.000 description 1
- HUSYTLMIRXITQS-UHFFFAOYSA-N 1,3-benzodioxole-5-carboxamide Chemical compound NC(=O)C1=CC=C2OCOC2=C1 HUSYTLMIRXITQS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/424,080 US3962259A (en) | 1973-12-12 | 1973-12-12 | 1,3-Dihydrospiro[isobenzofuran]s and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2458176A1 true DE2458176A1 (de) | 1975-06-26 |
Family
ID=23681366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742458176 Withdrawn DE2458176A1 (de) | 1973-12-12 | 1974-12-09 | Substituierte 1,3-dihydrospiro eckige klammer auf isobenzofurane eckige klammer zu |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US3962259A (en, 2012) |
| JP (1) | JPS5089363A (en, 2012) |
| AT (2) | AT352125B (en, 2012) |
| BE (1) | BE823279A (en, 2012) |
| CA (1) | CA1051886A (en, 2012) |
| CH (2) | CH620214A5 (en, 2012) |
| DE (1) | DE2458176A1 (en, 2012) |
| DK (1) | DK142055B (en, 2012) |
| FR (1) | FR2254332B1 (en, 2012) |
| GB (1) | GB1495286A (en, 2012) |
| IE (1) | IE40297B1 (en, 2012) |
| IL (1) | IL46202A (en, 2012) |
| LU (1) | LU71460A1 (en, 2012) |
| NL (1) | NL7415940A (en, 2012) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004952A1 (de) * | 1978-04-14 | 1979-10-31 | Hoechst Aktiengesellschaft | Spiro-(dihydrobenzofuranpiperidine und -pyrrolidine) und deren Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung für Arzneimittel |
| EP0004951A1 (de) * | 1978-04-14 | 1979-10-31 | Hoechst Aktiengesellschaft | N-(3-Benzoyl-propyl)-spiro-(dihydrobenzofuranpiperidine und -pyrrolidine) und Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung für Arzneimittel |
| EP0450761A1 (en) * | 1990-03-02 | 1991-10-09 | Merck & Co. Inc. | Spirocyclic oxytocin antagonists |
| EP0518805A1 (en) * | 1991-06-13 | 1992-12-16 | H. Lundbeck A/S | Piperidine derivatives |
| US5648352A (en) * | 1991-09-13 | 1997-07-15 | Merck & Co., Inc. | Piperazinylcamphorsulfonyl oxytocin antagonists |
| US5693643A (en) * | 1991-09-16 | 1997-12-02 | Merck & Co., Inc. | Hydantoin and succinimide-substituted derivatives of spiroindanylcamphorsulfonyl oxytocin antagonists |
| US8193208B2 (en) | 2005-09-09 | 2012-06-05 | Purdue Pharma L.P. | Fused and spirocycle compounds and the use thereof |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4241071A (en) * | 1977-01-27 | 1980-12-23 | American Hoechst Corporation | Antidepressant (α-phenyl-2-tolyl)azacycloalkanes |
| US4301292A (en) * | 1979-09-06 | 1981-11-17 | Hoechst-Roussel Pharmaceuticals, Incorporated | 1-[2-(4,5-Dihydro-4,4-dialkyl-2-oxazolyl)phenyl]-4-(dialkylamino)cyclohexanol |
| US4263317A (en) * | 1979-09-06 | 1981-04-21 | Hoechst-Roussel Pharmaceuticals, Inc. | Spiro[cyclohexane-1,1'(3'H)-isobenzofuran]s |
| US4268515A (en) * | 1980-02-04 | 1981-05-19 | Hoechst-Roussel Pharmaceuticals Inc. | Spiro[dihydrobenzofuran-piperidines and-pyrrolidines], pharmaceutical compositions thereof and methods of use thereof |
| FR2519636A2 (en) * | 1982-01-14 | 1983-07-18 | Delalande Sa | Spiro iso:benzofuran and iso:benzothiophene derivs. - with anticonvulsant and analgesic activities |
| FR2498603A1 (fr) * | 1981-01-29 | 1982-07-30 | Delalande Sa | Nouveaux derives spiro-1 isobenzofuranniques et spiro-1 isobenzothiopheniques, leur procede de preparation et leur application en therapeutique |
| US4374137A (en) * | 1981-08-07 | 1983-02-15 | Hoechst-Roussel Pharmaceuticals Inc. | Spiro[benzofuranisoquinoline]s and their use as pharmaceuticals |
| US4452802A (en) * | 1983-08-25 | 1984-06-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Antihypertensive spiro[benzofuran-azalkanes] |
| IL96507A0 (en) * | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
| US5206240A (en) * | 1989-12-08 | 1993-04-27 | Merck & Co., Inc. | Nitrogen-containing spirocycles |
| DK78692D0 (da) * | 1992-06-12 | 1992-06-12 | Lundbeck & Co As H | Dimere piperidin- og piperazinderivater |
| US5239110A (en) * | 1992-12-30 | 1993-08-24 | Sterling Winthrop, Inc. | Phenylcyclohexanol derivatives as agents for treating CNS disorders |
| WO1995028389A1 (fr) * | 1994-04-15 | 1995-10-26 | Yamanouchi Pharmaceutical Co., Ltd. | Compose spiro et composition medicinale issue de ce compose |
| US6017919A (en) * | 1996-02-06 | 2000-01-25 | Japan Tobacco Inc. | Compounds and pharmaceutical use thereof |
| US6374762B1 (en) * | 1997-10-27 | 2002-04-23 | Correct Craft, Inc. | Water sport towing apparatus |
| ES2235368T3 (es) * | 1997-10-27 | 2005-07-01 | Sumitomo Pharmaceuticals Company, Limited | Derivados de amida para tratar alteraciones neurodegenerativas de la retina. |
| US6166209A (en) * | 1997-12-11 | 2000-12-26 | Hoffmann-La Roche Inc. | Piperidine derivatives |
| AU3837800A (en) * | 1999-04-21 | 2000-11-10 | Sumitomo Pharmaceuticals Company, Limited | Amide derivatives |
| AU3679800A (en) * | 1999-04-23 | 2000-11-10 | Sumitomo Pharmaceuticals Company, Limited | Apoptosis inhibitors |
| WO2002034719A1 (fr) * | 2000-04-21 | 2002-05-02 | Sankyo Company, Limited | Composes heterocycliques azotes satures |
| US20030078278A1 (en) * | 2001-06-26 | 2003-04-24 | Pfizer Inc. | Spiropiperidine compounds as ligands for ORL-1 receptor |
| US7786141B2 (en) * | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| CA2577677A1 (en) | 2004-08-19 | 2006-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| WO2006058303A2 (en) * | 2004-11-29 | 2006-06-01 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| CA2634456A1 (en) * | 2005-12-22 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| CN101426499A (zh) | 2006-02-22 | 2009-05-06 | 弗特克斯药品有限公司 | 毒蕈碱受体调节剂 |
| KR20080098070A (ko) * | 2006-02-22 | 2008-11-06 | 버텍스 파마슈티칼스 인코포레이티드 | 무스카린성 수용체의 조절제로서의 스피로 축합된 피페리딘 |
| EP1847542A1 (en) * | 2006-04-21 | 2007-10-24 | Laboratorios del Dr. Esteve S.A. | Spiro[benzopyran] or spiro[benzofuran] derivatives which inhibit the sigma receptor |
| WO2008005295A2 (en) * | 2006-06-29 | 2008-01-10 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| WO2008021375A2 (en) * | 2006-08-15 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| CN101573121A (zh) * | 2006-08-18 | 2009-11-04 | 弗特克斯药品有限公司 | 毒蕈碱受体调节剂 |
| MX2010003373A (es) * | 2007-10-03 | 2010-04-30 | Vertex Pharma | Moduladores de receptores muscarinicos. |
| EP2563764B1 (en) * | 2010-04-26 | 2015-02-25 | Merck Sharp & Dohme Corp. | Novel spiropiperidine prolylcarboxypeptidase inhibitors |
| TWI543984B (zh) | 2010-07-09 | 2016-08-01 | 艾伯維公司 | 作為s1p調節劑的螺-哌啶衍生物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686186A (en) * | 1970-10-05 | 1972-08-22 | William J Houlihan | Substituted isochroman or phthalan piperidenes |
-
1973
- 1973-12-12 US US05/424,080 patent/US3962259A/en not_active Expired - Lifetime
-
1974
- 1974-12-06 NL NL7415940A patent/NL7415940A/xx not_active Application Discontinuation
- 1974-12-06 IL IL46202A patent/IL46202A/xx unknown
- 1974-12-09 DE DE19742458176 patent/DE2458176A1/de not_active Withdrawn
- 1974-12-11 CA CA215,785A patent/CA1051886A/en not_active Expired
- 1974-12-11 DK DK645074AA patent/DK142055B/da unknown
- 1974-12-11 IE IE2547/74A patent/IE40297B1/en unknown
- 1974-12-11 LU LU71460A patent/LU71460A1/xx unknown
- 1974-12-11 AT AT988374A patent/AT352125B/de not_active IP Right Cessation
- 1974-12-11 CH CH1646974A patent/CH620214A5/de not_active IP Right Cessation
- 1974-12-12 JP JP49142998A patent/JPS5089363A/ja active Pending
- 1974-12-12 BE BE151443A patent/BE823279A/xx unknown
- 1974-12-12 GB GB53743/74A patent/GB1495286A/en not_active Expired
- 1974-12-12 FR FR7441007A patent/FR2254332B1/fr not_active Expired
-
1975
- 1975-07-01 US US05/592,214 patent/US3985889A/en not_active Expired - Lifetime
-
1977
- 1977-11-14 AT AT0812377A patent/AT365191B/de not_active IP Right Cessation
-
1979
- 1979-06-26 CH CH596979A patent/CH624407A5/de not_active IP Right Cessation
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004952A1 (de) * | 1978-04-14 | 1979-10-31 | Hoechst Aktiengesellschaft | Spiro-(dihydrobenzofuranpiperidine und -pyrrolidine) und deren Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung für Arzneimittel |
| EP0004951A1 (de) * | 1978-04-14 | 1979-10-31 | Hoechst Aktiengesellschaft | N-(3-Benzoyl-propyl)-spiro-(dihydrobenzofuranpiperidine und -pyrrolidine) und Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung für Arzneimittel |
| EP0450761A1 (en) * | 1990-03-02 | 1991-10-09 | Merck & Co. Inc. | Spirocyclic oxytocin antagonists |
| EP0518805A1 (en) * | 1991-06-13 | 1992-12-16 | H. Lundbeck A/S | Piperidine derivatives |
| US5648352A (en) * | 1991-09-13 | 1997-07-15 | Merck & Co., Inc. | Piperazinylcamphorsulfonyl oxytocin antagonists |
| US5693643A (en) * | 1991-09-16 | 1997-12-02 | Merck & Co., Inc. | Hydantoin and succinimide-substituted derivatives of spiroindanylcamphorsulfonyl oxytocin antagonists |
| US8193208B2 (en) | 2005-09-09 | 2012-06-05 | Purdue Pharma L.P. | Fused and spirocycle compounds and the use thereof |
| US8546417B2 (en) | 2005-09-09 | 2013-10-01 | Purdue Pharma L.P. | Fused and spirocycle compounds and the use thereof |
| US8883816B2 (en) | 2005-09-09 | 2014-11-11 | Purdue Pharma L.P. | Fused and spirocycle compounds and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DK142055C (en, 2012) | 1981-01-12 |
| IL46202A0 (en) | 1975-03-13 |
| NL7415940A (nl) | 1975-06-16 |
| CH624407A5 (en, 2012) | 1981-07-31 |
| DK645074A (en, 2012) | 1975-08-18 |
| AT365191B (de) | 1981-12-28 |
| US3962259A (en) | 1976-06-08 |
| FR2254332A1 (en, 2012) | 1975-07-11 |
| JPS5089363A (en, 2012) | 1975-07-17 |
| CH620214A5 (en, 2012) | 1980-11-14 |
| CA1051886A (en) | 1979-04-03 |
| ATA988374A (de) | 1979-02-15 |
| ATA812377A (de) | 1981-05-15 |
| BE823279A (en, 2012) | 1975-06-12 |
| AT352125B (de) | 1979-09-10 |
| US3985889A (en) | 1976-10-12 |
| IE40297B1 (en) | 1979-04-25 |
| DK142055B (da) | 1980-08-18 |
| IL46202A (en) | 1980-02-29 |
| GB1495286A (en) | 1977-12-14 |
| LU71460A1 (en, 2012) | 1976-11-11 |
| FR2254332B1 (en, 2012) | 1978-07-21 |
| IE40297L (en) | 1975-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification | ||
| 8130 | Withdrawal |