CS157191A3 - Pyrrido/3,4-b/pyrrolo/1,2-e//1,4,5/oxadiazepines - Google Patents

Pyrrido/3,4-b/pyrrolo/1,2-e//1,4,5/oxadiazepines Download PDF

Info

Publication number: CS157191A3
Authority: CS; Czechoslovakia
Prior art keywords: lower alkyl; hydrogen; compound; methyl; pyrrolo
Prior art date: 1990-05-25

Application number

CS911571A

Other languages

Czech (cs)

English (en)

Inventor

Richard C Effland

Larry Davis

Original Assignee

Hoechst Roussel Pharma

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.)

1990-05-25

Filing date

1991-05-24

Publication date

1992-01-15

1991-05-24 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1992-01-15 Publication of CS157191A3 publication Critical patent/CS157191A3/cs

Links

150000001875 compounds Chemical class 0.000 claims abstract description 37
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract 9
125000000217 alkyl group Chemical group 0.000 claims description 22
-1 1-methyl-4-piperidinyl Chemical group 0.000 claims description 16
RYDICHIKLKVOEJ-UHFFFAOYSA-N oxadiazepine Chemical compound O1C=CC=CN=N1 RYDICHIKLKVOEJ-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
239000002671 adjuvant Substances 0.000 claims 1
230000000202 analgesic effect Effects 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000730 antalgic agent Substances 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000003921 oil Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000007787 solid Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 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
230000000694 effects Effects 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
KNUGDJLHNWPBFA-UHFFFAOYSA-N 1-[(3-fluoropyridin-4-yl)methylamino]pyrrole-2-carbaldehyde Chemical compound FC1=CN=CC=C1CNN1C(C=O)=CC=C1 KNUGDJLHNWPBFA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 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
CPRHIHPBBWWOOI-UHFFFAOYSA-N [1-[(3-fluoropyridin-4-yl)methylamino]pyrrol-2-yl]methanol Chemical compound OCC1=CC=CN1NCC1=CC=NC=C1F CPRHIHPBBWWOOI-UHFFFAOYSA-N 0.000 description 2
238000003556 assay Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000006187 pill Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000002265 prevention Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose 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
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
NNHCFSLBNPIGQO-UHFFFAOYSA-N 1,4,5-oxadiazepine Chemical compound O1C=CN=NC=C1 NNHCFSLBNPIGQO-UHFFFAOYSA-N 0.000 description 1
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 1
BEQUUSCRAKEKQM-UHFFFAOYSA-N 4-chloro-3-fluoropyridine Chemical compound FC1=CN=CC=C1Cl BEQUUSCRAKEKQM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
QVORIRSXZDGVBD-UHFFFAOYSA-N C12=CC=CN2N(C)C2=CC=NC=C2OC1C1CCNCC1 Chemical compound C12=CC=CN2N(C)C2=CC=NC=C2OC1C1CCNCC1 QVORIRSXZDGVBD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
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241000124008 Mammalia Species 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910017917 NH4 Cl Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
210000003815 abdominal wall Anatomy 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
238000012466 analgesic assay Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 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
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
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150000004795 grignard reagents Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
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230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
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238000012417 linear regression Methods 0.000 description 1
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239000008108 microcrystalline cellulose Substances 0.000 description 1
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XDBORIMSNLCXQK-UHFFFAOYSA-N n-methylpyrrol-1-amine Chemical compound CNN1C=CC=C1 XDBORIMSNLCXQK-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—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
- A61P25/04—Centrally acting analgesics, e.g. opioids

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

CS911571A 1990-05-25 1991-05-24 Pyrrido/3,4-b/pyrrolo/1,2-e//1,4,5/oxadiazepines CS157191A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/529,082 US5015637A (en)	1990-05-25	1990-05-25	Pyrido[3,4-b]pyrrolo[1,2-e][1,4,5]oxadiazepines

Publications (1)

Publication Number	Publication Date
CS157191A3 true CS157191A3 (en)	1992-01-15

Family

ID=24108456

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911571A CS157191A3 (en)	1990-05-25	1991-05-24	Pyrrido/3,4-b/pyrrolo/1,2-e//1,4,5/oxadiazepines

Country Status (22)

Country	Link
US (1)	US5015637A (de)
EP (1)	EP0458331B1 (de)
JP (1)	JP3090500B2 (de)
KR (1)	KR100286405B1 (de)
AT (1)	ATE183746T1 (de)
AU (1)	AU638572B2 (de)
CA (1)	CA2043229C (de)
CS (1)	CS157191A3 (de)
DE (1)	DE69131546T2 (de)
DK (1)	DK0458331T3 (de)
ES (1)	ES2135383T3 (de)
FI (1)	FI912499L (de)
GR (1)	GR3031538T3 (de)
HU (1)	HU207520B (de)
IE (1)	IE911788A1 (de)
IL (1)	IL98231A (de)
MX (1)	MX25922A (de)
NO (1)	NO911998L (de)
NZ (1)	NZ238238A (de)
PL (1)	PL290405A1 (de)
PT (1)	PT97762B (de)
ZA (1)	ZA913951B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2333691T3 (es) *	1993-05-27	2010-02-26	Board Of Regents Of The University Of Washington	Union a gmp ciclica, materiales de fosfodiesterasa especificos a gmp ciclicos y metodos.
AR037853A1 (es) *	2001-12-18	2004-12-09	Syngenta Participations Ag	Proceso para la preparacion de derivados de [1,4,5]-oxadiazepinas, y empleo de esos derivados en la preparacion de un herbicida del tipo de la tetrahidropirazolodiona
KR20130072194A (ko)	2010-04-18	2013-07-01	유창준	위치조절이 가능한 삽입물을 갖는 베개

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4029672A (en) *	1976-02-26	1977-06-14	American Hoechst Corporation	Aminoalkylpyrrolobenzoxazalkanes
US4045448A (en) *	1976-02-26	1977-08-30	American Hoechst Corporation	Pyrrolo[2,1-c][1,4]benzoxazepine and benzoxazocine derivatives
FI803908L (fi) *	1979-12-21	1981-06-22	Sandoz Ag	Nya pyrrolobenszotriazepiner deras framstaellning och dessa innehaollande farmaceutiska foereningar
US4608374A (en) *	1983-11-07	1986-08-26	Hoechst-Roussel Pharmaceuticals Inc.	11-substituted 5H,11H-pyrrolo[2,1-c][1,4]benzoxazepines as antipsychotic and analgesic agents
US4794110A (en) *	1987-07-20	1988-12-27	Hoechst-Roussel Pharmaceuticals, Inc.	5-Aryl-11-substituted-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepined as analgesic and hypotensive agents
US4879382A (en) *	1988-07-25	1989-11-07	Hoechst-Roussel Pharmaceuticals, Inc.	Pyrido(3,4-f)pyrrolo(1,2-b)(1,2,5)triazepines

1990
- 1990-05-25 US US07/529,082 patent/US5015637A/en not_active Expired - Fee Related
1991
- 1991-04-29 AU AU76213/91A patent/AU638572B2/en not_active Expired - Fee Related
- 1991-05-23 NZ NZ238238A patent/NZ238238A/xx unknown
- 1991-05-23 AT AT91108348T patent/ATE183746T1/de not_active IP Right Cessation
- 1991-05-23 EP EP91108348A patent/EP0458331B1/de not_active Expired - Lifetime
- 1991-05-23 FI FI912499A patent/FI912499L/fi unknown
- 1991-05-23 DK DK91108348T patent/DK0458331T3/da active
- 1991-05-23 DE DE69131546T patent/DE69131546T2/de not_active Expired - Fee Related
- 1991-05-23 IL IL9823191A patent/IL98231A/en unknown
- 1991-05-23 KR KR1019910008298A patent/KR100286405B1/ko not_active Expired - Fee Related
- 1991-05-23 ES ES91108348T patent/ES2135383T3/es not_active Expired - Lifetime
- 1991-05-24 HU HU911755A patent/HU207520B/hu not_active IP Right Cessation
- 1991-05-24 IE IE178891A patent/IE911788A1/en not_active IP Right Cessation
- 1991-05-24 CS CS911571A patent/CS157191A3/cs unknown
- 1991-05-24 PT PT97762A patent/PT97762B/pt not_active IP Right Cessation
- 1991-05-24 NO NO91911998A patent/NO911998L/no unknown
- 1991-05-24 MX MX2592291A patent/MX25922A/es unknown
- 1991-05-24 JP JP03148201A patent/JP3090500B2/ja not_active Expired - Fee Related
- 1991-05-24 PL PL29040591A patent/PL290405A1/xx unknown
- 1991-05-24 CA CA002043229A patent/CA2043229C/en not_active Expired - Fee Related
- 1991-05-24 ZA ZA913951A patent/ZA913951B/xx unknown
1999
- 1999-10-15 GR GR990402625T patent/GR3031538T3/el unknown

Also Published As

Publication number	Publication date
FI912499A7 (fi)	1991-11-26
EP0458331B1 (de)	1999-08-25
IL98231A0 (en)	1992-06-21
FI912499L (fi)	1991-11-26
MX25922A (es)	1993-10-01
NZ238238A (en)	1993-06-25
AU7621391A (en)	1991-11-28
HU207520B (en)	1993-04-28
DE69131546T2 (de)	2000-03-23
ES2135383T3 (es)	1999-11-01
HU911755D0 (en)	1991-12-30
KR100286405B1 (ko)	2001-04-16
CA2043229A1 (en)	1991-11-26
IL98231A (en)	1994-11-28
IE911788A1 (en)	1991-12-04
DE69131546D1 (de)	1999-09-30
PT97762B (pt)	1998-10-30
AU638572B2 (en)	1993-07-01
PL290405A1 (en)	1992-08-24
PT97762A (pt)	1992-02-28
ZA913951B (en)	1992-03-25
JP3090500B2 (ja)	2000-09-18
JPH04235186A (ja)	1992-08-24
KR910020018A (ko)	1991-12-19
EP0458331A1 (de)	1991-11-27
GR3031538T3 (en)	2000-01-31
ATE183746T1 (de)	1999-09-15
NO911998L (no)	1991-11-26
NO911998D0 (no)	1991-05-24
US5015637A (en)	1991-05-14
CA2043229C (en)	2003-02-11
HUT60744A (en)	1992-10-28
DK0458331T3 (da)	2000-03-13
FI912499A0 (fi)	1991-05-23

Publication	Publication Date	Title
US6001847A (en)	1999-12-14	Chemical compounds
RU2136682C1 (ru)	1999-09-10	Имидазопиридины, способ их получения, фармацевтическая композиция на их основе и способ получения фармацевтической композиции
EP2686320B1 (de)	2016-05-18	Tricyclische gyrase-inhibitoren
KR970009588B1 (ko)	1997-06-14	헤테로사이클릭 화합물
DE69221059T2 (de)	1997-11-13	Indolderivate und antiulcerose Zubereitungen
RU2548363C2 (ru)	2015-04-20	СЕЛЕКТИВНЫЕ ИНГИБИТОРЫ Haspin киназы
ES2734268T3 (es)	2019-12-05	Derivados de urea y amida de aminoalquilpiperazinas y uso de los mismos
TW201141483A (en)	2011-12-01	Thienopyrimidines containing a substituted alkyl group for pharmaceutical compositions
DE69433148T2 (de)	2004-06-03	Tricyclische kondensierte heterocyclische Verbindungen zur Behandlung von seniler Demenz
DE60310767T2 (de)	2007-10-11	PYRAZOL-3,4-d-PYRIMIDINDERIVATE UND IHRE VERWENDUNG BEI DER BEHANDLUNG VON H.PYLORI-INFEKTIONEN
US6960585B2 (en)	2005-11-01	Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same
US3594380A (en)	1971-07-20	Isoquinolin-1(2h)-ones
US4824848A (en)	1989-04-25	Pyrazolo[3,4-d]pyrimidine derivatives, their production and use
EP0874849B1 (de)	2001-09-19	2,7-SUBSTITUIERTE OCTAHYDROPYRROLO(1,2-a)PYRAZINDERIVATE
US6346531B1 (en)	2002-02-12	G-CSF mimetics
US6630470B1 (en)	2003-10-07	G-CSF mimetics
JPS6030677B2 (ja)	1985-07-17	新規な６−フェニル−４Ｈ−イミダゾ〔１，２−α〕〔１，４〕ベンゾジアゼピン類の製造方法
FI71936C (fi)	1987-03-09	Foerfarande foer framstaellning av neuroleptiskt aktiva 2-substituerade-8-fluor-5-(4-fluorfenyl)-2,3,4,4a, 5,9b-hexahydro-4a,9b-trans-1h-pyrido/4,3-b/indolderivat.
KR950010073B1 (ko)	1995-09-06	치환된 피리도[2,3-b][1,4]벤조디아제핀-6-온, 이의 제조방법 및 이를 함유하는 약제
CS157191A3 (en)	1992-01-15	Pyrrido/3,4-b/pyrrolo/1,2-e//1,4,5/oxadiazepines
US4728649A (en)	1988-03-01	3-oxo-piperazin-1-yl-ergolines exhibiting antidopaminergic activity
IE903616A1 (en)	1991-04-24	Neuroprotectant Agents
US3852446A (en)	1974-12-03	Organic compounds in treatment of psychotic disturbances
JPS6310788A (ja)	1988-01-18	３−アミノピラゾロ〔３，４−ｄ〕ピリミジン誘導体
US4077955A (en)	1978-03-07	Amino derivatives of 1,2,3,4-tetrahydro-2-oxopyrido[2,2-b]-pyrazine carboxylic acids and esters