NL7909025A - Nieuwe cyclododecaanderivaten en werkwijze voor de bereiding van deze derivaten. - Google Patents

Nieuwe cyclododecaanderivaten en werkwijze voor de bereiding van deze derivaten. Download PDF

Info

Publication number: NL7909025A
Authority: NL; Netherlands
Prior art keywords: general formula; derivative; group; cyclododecane; mol
Prior art date: 1978-12-19

Application number

NL7909025A

Other languages

English (en)

Dutch (nl)

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1978-12-19

Filing date

1979-12-14

Publication date

1980-06-23

1979-12-14 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1980-06-23 Publication of NL7909025A publication Critical patent/NL7909025A/nl

Links

DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical class C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims description 35
SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical class O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 claims description 17
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 10
229910000104 sodium hydride Inorganic materials 0.000 claims description 10
239000012312 sodium hydride Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
239000013543 active substance Substances 0.000 claims description 8
-1 alkali metal alkoxide Chemical class 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 11
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 description 10
239000008298 dragée Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000008120 corn starch Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
239000007903 gelatin capsule Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229960001789 papaverine Drugs 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MTWNJKFHMFBTMG-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(cyclododecylideneamino)oxy-n,n-diethylethanamine Chemical compound OC(=O)\C=C\C(O)=O.CCN(CC)CCON=C1CCCCCCCCCCC1 MTWNJKFHMFBTMG-WLHGVMLRSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
YFIASDXULNXOAZ-UHFFFAOYSA-N 2-(cyclododecylideneamino)oxy-n,n-diethylethanamine Chemical compound CCN(CC)CCON=C1CCCCCCCCCCC1 YFIASDXULNXOAZ-UHFFFAOYSA-N 0.000 description 2
LUDVXWQMOSWOKZ-UHFFFAOYSA-N 3-(cyclododecylideneamino)oxy-n,n-di(propan-2-yl)propan-1-amine Chemical compound CC(C)N(C(C)C)CCCON=C1CCCCCCCCCCC1 LUDVXWQMOSWOKZ-UHFFFAOYSA-N 0.000 description 2
VPBZETYBRLPLSN-UHFFFAOYSA-N 3-(cyclododecylideneamino)oxy-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCON=C1CCCCCCCCCCC1 VPBZETYBRLPLSN-UHFFFAOYSA-N 0.000 description 2
HJDKXIDZVWPKSY-UHFFFAOYSA-N 3-(cyclododecylideneamino)oxy-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCON=C1CCCCCCCCCCC1 HJDKXIDZVWPKSY-UHFFFAOYSA-N 0.000 description 2
UGXACBBAXFABGT-UHFFFAOYSA-N 3-chloro-n,n,2-trimethylpropan-1-amine Chemical compound ClCC(C)CN(C)C UGXACBBAXFABGT-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229960004194 lidocaine Drugs 0.000 description 2
239000003589 local anesthetic agent Substances 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
IRSNFALUAOOYBR-UHFFFAOYSA-N n-[2-(cyclododecylideneamino)oxyethyl]-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCON=C1CCCCCCCCCCC1 IRSNFALUAOOYBR-UHFFFAOYSA-N 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
DUUQDDTXKQABSD-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-(cyclododecylideneamino)oxy-n,n-di(propan-2-yl)propan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.CC(C)N(C(C)C)CCCON=C1CCCCCCCCCCC1 DUUQDDTXKQABSD-WLHGVMLRSA-N 0.000 description 1
WXAGQEZVNSJKCU-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-(cyclododecylideneamino)oxy-n,n-dimethylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCCON=C1CCCCCCCCCCC1 WXAGQEZVNSJKCU-WLHGVMLRSA-N 0.000 description 1
FQJDUWXFZXKOSV-UHFFFAOYSA-N 1-benzyl-2-(3-chloropropyl)piperazine Chemical compound ClCCCC1CNCCN1CC1=CC=CC=C1 FQJDUWXFZXKOSV-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
VTJALIBWBDVIMV-UHFFFAOYSA-N 2-(3-chloropropyl)-1-methylpiperazine Chemical compound CN1CCNCC1CCCCl VTJALIBWBDVIMV-UHFFFAOYSA-N 0.000 description 1
NVGXXXNUGIYECN-UHFFFAOYSA-N 2-(cyclododecylideneamino)oxy-n,n-dimethylethanamine Chemical compound CN(C)CCON=C1CCCCCCCCCCC1 NVGXXXNUGIYECN-UHFFFAOYSA-N 0.000 description 1
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
SVLPIZNVKGEAET-UHFFFAOYSA-N 3-(cyclododecylideneamino)oxy-n,n-diethyl-2-methylpropan-1-amine Chemical compound CCN(CC)CC(C)CON=C1CCCCCCCCCCC1 SVLPIZNVKGEAET-UHFFFAOYSA-N 0.000 description 1
RXYQHVMJQFHKDX-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine Chemical compound CC(C)N(C(C)C)CCCCl RXYQHVMJQFHKDX-UHFFFAOYSA-N 0.000 description 1
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
XOWFSFWINAZCIO-WLHGVMLRSA-N C(\C=C\C(=O)O)(=O)O.C1CCCCCCCCCCC1 Chemical compound C(\C=C\C(=O)O)(=O)O.C1CCCCCCCCCCC1 XOWFSFWINAZCIO-WLHGVMLRSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RAAYMGBLVONKGM-UHFFFAOYSA-N Cl.Cl.Cl.CNOCCCN1CCNCC1 Chemical compound Cl.Cl.Cl.CNOCCCN1CCNCC1 RAAYMGBLVONKGM-UHFFFAOYSA-N 0.000 description 1
YCJTZVDRNMJJEW-UHFFFAOYSA-N Cl.O1CCN(CC1)CCCON Chemical compound Cl.O1CCN(CC1)CCCON YCJTZVDRNMJJEW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000000648 anti-parkinson Effects 0.000 description 1
230000000794 anti-serotonin Effects 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
239000000939 antiparkinson agent Substances 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
FYYHWMGAXLPEAU-OUBTZVSYSA-N magnesium-25 atom Chemical compound [25Mg] FYYHWMGAXLPEAU-OUBTZVSYSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
208000022084 motor paralysis Diseases 0.000 description 1
DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 1
YLHVAEAZZXGNIC-UHFFFAOYSA-N n-(3-chloropropyl)-n-methylcyclohexanamine Chemical compound ClCCCN(C)C1CCCCC1 YLHVAEAZZXGNIC-UHFFFAOYSA-N 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
FSOIPIOEMIUMPV-UHFFFAOYSA-N o-[1-(diethylamino)-2-methylpropyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CCN(CC)C(ON)C(C)C FSOIPIOEMIUMPV-UHFFFAOYSA-N 0.000 description 1
JGLYFEDZRXNSGB-UHFFFAOYSA-N o-[2-(diethylamino)ethyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CCN(CC)CCON JGLYFEDZRXNSGB-UHFFFAOYSA-N 0.000 description 1
UBVSMBHQHHGRSR-UHFFFAOYSA-N o-[2-(dimethylamino)ethyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CN(C)CCON UBVSMBHQHHGRSR-UHFFFAOYSA-N 0.000 description 1
YFLJCNQZTVAVOI-UHFFFAOYSA-N o-[2-[di(propan-2-yl)amino]ethyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CC(C)N(C(C)C)CCON YFLJCNQZTVAVOI-UHFFFAOYSA-N 0.000 description 1
IWCIDSAYQRVUOI-UHFFFAOYSA-N o-[3-(diethylamino)propyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CCN(CC)CCCON IWCIDSAYQRVUOI-UHFFFAOYSA-N 0.000 description 1
MPSCWZFDRCEEEO-UHFFFAOYSA-N o-[3-[di(propan-2-yl)amino]propyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CC(C)N(C(C)C)CCCON MPSCWZFDRCEEEO-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
210000003497 sciatic nerve Anatomy 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)

NL7909025A 1978-12-19 1979-12-14 Nieuwe cyclododecaanderivaten en werkwijze voor de bereiding van deze derivaten. NL7909025A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU78EE2614A HU178518B (en)	1978-12-19	1978-12-19	Process for preparing cyclododekanone oxime ethers
HUEE002614		1978-12-19

Publications (1)

Publication Number	Publication Date
NL7909025A true NL7909025A (nl)	1980-06-23

Family

ID=10995810

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7909025A NL7909025A (nl)	1978-12-19	1979-12-14	Nieuwe cyclododecaanderivaten en werkwijze voor de bereiding van deze derivaten.

Country Status (24)

Country	Link
US (1)	US4285942A (cs)
JP (1)	JPS55108847A (cs)
AT (1)	AT372079B (cs)
AU (1)	AU530721B2 (cs)
BE (1)	BE880508A (cs)
CA (1)	CA1123852A (cs)
CH (1)	CH647755A5 (cs)
CS (1)	CS209944B2 (cs)
DD (1)	DD148216A5 (cs)
DE (1)	DE2951235A1 (cs)
DK (1)	DK541079A (cs)
ES (1)	ES8100257A1 (cs)
FI (1)	FI793964A7 (cs)
FR (1)	FR2444666A1 (cs)
GB (1)	GB2045744B (cs)
GR (1)	GR74018B (cs)
HU (1)	HU178518B (cs)
IL (1)	IL58815A (cs)
IT (1)	IT1220957B (cs)
NL (1)	NL7909025A (cs)
PL (1)	PL120041B1 (cs)
SE (1)	SE7910430L (cs)
SU (1)	SU833157A3 (cs)
YU (2)	YU308479A (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU189226B (en) *	1983-02-08	1986-06-30	Egyt Gyogyszervegyeszeti Gyar,Hu	Process for producing basic oxime-ethers
HU212262B (en) *	1992-10-30	1996-04-29	Egyt Gyogyszervegyeszeti Gyar	Process to prepare benz /e/ indene derivs. and the pharmaceutical compns. contg. them
US5508302A (en) *	1994-09-28	1996-04-16	American Home Products Corporation	Phospholipase A2 inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1733462A (en) *	1926-09-23	1929-10-29	Winthrop Chem Co Inc	New basic oxime ethers of cyclic compounds
US4083978A (en) *	1976-01-27	1978-04-11	Egyt Gyogyszervegyeszeti Gyar	Oxime ethers

1978
- 1978-12-19 HU HU78EE2614A patent/HU178518B/hu not_active IP Right Cessation
1979
- 1979-11-27 IL IL58815A patent/IL58815A/xx unknown
- 1979-12-03 AT AT0765379A patent/AT372079B/de not_active IP Right Cessation
- 1979-12-03 US US06/099,507 patent/US4285942A/en not_active Expired - Lifetime
- 1979-12-03 GR GR60658A patent/GR74018B/el unknown
- 1979-12-07 CS CS798554A patent/CS209944B2/cs unknown
- 1979-12-10 FR FR7930183A patent/FR2444666A1/fr active Granted
- 1979-12-10 BE BE1/9638A patent/BE880508A/fr not_active IP Right Cessation
- 1979-12-13 DD DD79217646A patent/DD148216A5/de unknown
- 1979-12-14 NL NL7909025A patent/NL7909025A/nl not_active Application Discontinuation
- 1979-12-17 YU YU03084/79A patent/YU308479A/xx unknown
- 1979-12-17 IT IT28029/79A patent/IT1220957B/it active
- 1979-12-18 SU SU792855002A patent/SU833157A3/ru active
- 1979-12-18 DK DK541079A patent/DK541079A/da not_active Application Discontinuation
- 1979-12-18 FI FI793964A patent/FI793964A7/fi not_active Application Discontinuation
- 1979-12-18 GB GB7943550A patent/GB2045744B/en not_active Expired
- 1979-12-18 SE SE7910430A patent/SE7910430L/xx not_active Application Discontinuation
- 1979-12-18 CH CH11197/79A patent/CH647755A5/de not_active IP Right Cessation
- 1979-12-18 AU AU53967/79A patent/AU530721B2/en not_active Ceased
- 1979-12-19 CA CA342,285A patent/CA1123852A/en not_active Expired
- 1979-12-19 PL PL1979220531A patent/PL120041B1/pl unknown
- 1979-12-19 ES ES487090A patent/ES8100257A1/es not_active Expired
- 1979-12-19 JP JP16416379A patent/JPS55108847A/ja active Pending
- 1979-12-19 DE DE19792951235 patent/DE2951235A1/de not_active Withdrawn
1983
- 1983-04-21 YU YU00912/83A patent/YU91283A/xx unknown

Also Published As

Publication number	Publication date
PL220531A1 (cs)	1980-08-25
IT7928029A0 (it)	1979-12-17
US4285942A (en)	1981-08-25
AT372079B (de)	1983-08-25
AU530721B2 (en)	1983-07-28
AU5396779A (en)	1980-06-26
BE880508A (fr)	1980-06-10
GB2045744B (en)	1982-11-10
HU178518B (en)	1982-05-28
CA1123852A (en)	1982-05-18
FR2444666A1 (fr)	1980-07-18
ATA765379A (de)	1983-01-15
IT1220957B (it)	1990-06-21
YU91283A (en)	1983-12-31
CH647755A5 (de)	1985-02-15
GR74018B (cs)	1984-06-06
DD148216A5 (de)	1981-05-13
DK541079A (da)	1980-06-20
SU833157A3 (ru)	1981-05-23
JPS55108847A (en)	1980-08-21
IL58815A (en)	1984-01-31
ES487090A0 (es)	1980-11-01
SE7910430L (sv)	1980-06-20
DE2951235A1 (de)	1980-11-06
IL58815A0 (en)	1980-02-29
PL120041B1 (en)	1982-02-27
CS209944B2 (en)	1981-12-31
FR2444666B1 (cs)	1982-11-12
GB2045744A (en)	1980-11-05
YU308479A (en)	1983-12-31
ES8100257A1 (es)	1980-11-01
FI793964A7 (fi)	1981-01-01

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-02-02	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0591040B1 (fr)	1999-02-03	Amides basiques quaternaires comme antagonistes des tachykinines
US4474692A (en)	1984-10-02	L-Alanyl-N-(indan-2-yl)glycine, its esters and salts thereof
US20040220193A1 (en)	2004-11-04	Nitrogen-containing cyclic compound and pharmaceutical composition containing the compound
US5071859A (en)	1991-12-10	N-substituted azaheterocyclic carboxylic acids and pharmaceutical uses
HU187868B (en)	1986-02-28	Process for producing dihydropyridine derivatives
PL186773B1 (pl)	2004-02-27	Nowe pochodne benzyloaminopiperydyny i środek farmaceutyczny
SK279168B6 (sk)	1998-07-08	Bicyklické 1-azacykloalkány, farmaceutické prostri
EP2760829A1 (en)	2014-08-06	Pyrrolinone carboxamide compounds useful as endothelial lipase inhibitors
WO2013049096A1 (en)	2013-04-04	Pyrrolinone carboxamide compounds useful as endothelial lipase inhibitors
Acheson et al.	1980	Transformations involving the pyrrolidine ring of nicotine
US4604389A (en)	1986-08-05	Benzazepine derivatives
DE69329084T2 (de)	2000-12-21	Benzoxazepin-Derivate als Cholinesterase-Inhibitoren
Tenthorey et al.	1981	New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides
US4285942A (en)	1981-08-25	Cyclododecanone oximes
HU199774B (en)	1990-03-28	Process for production of derivatives of amin-alcohol and medical compositions containing them as active substance
FI86174C (fi)	1992-07-27	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara aminopropanolderivat av substituerade 2 -hydroxipropiofenoner.
KR100332325B1 (ko)	2002-09-04	이소프로필2-메톡시에틸4-(2-클로로-3-시아노-페닐)-1,4-디히디로-2,6-디메틸-피리딘-3,5-디카르복실레이트
FI65060B (fi)	1983-11-30	Foerfarande foer framstaellning av 4-metoxi-n-(2-(2-(1-metyl-2-piperidyl)etyl)fenyl)-bensamid-n-oxid som haemmar rytmstoerningar i hjaertat
CN121914118A (zh)	2026-04-24	一种吲哚二氮杂卓类衍生物的制备方法及应用
EP0619299A2 (en)	1994-10-12	1-(Phenyl)-3-[omega-(amino)-alkoxyimino]-alk-1-ene derivatives, a process for preparing them as well as medicaments containing them and the use of them
JPH07500571A (ja)	1995-01-19	Ｐｃｐレセプター・リガンドおよびその用途
FI67688B (fi)	1985-01-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara alanolaminderivat
DK167922B1 (da)	1994-01-03	Quinaldinamidderivater, en fremgangsmaade til deres fremstilling samt et farmaceutisk praeparat indeholdende et saadant derivat
JPS6143164A (ja)	1986-03-01	ピロリジンジオン誘導体
AU2005201992A1 (en)	2005-06-02	Nitrogenous cyclic compounds and pharmaceutical compositions containing the same