SK11122003A3 - Substituované dimetyl-[1-(1-fenyl-cyklohexyl)-piperidín-3- ylmetyl]-amíny, spôsob ich výroby, liečivá tieto látky obsahujúce a ich použitie - Google Patents

Substituované dimetyl-[1-(1-fenyl-cyklohexyl)-piperidín-3- ylmetyl]-amíny, spôsob ich výroby, liečivá tieto látky obsahujúce a ich použitie Download PDF

Info

Publication number: SK11122003A3
Authority: SK; Slovakia
Prior art keywords: phenyl; formula; cyclohexyl; piperidin; dimethylaminomethyl
Prior art date: 2001-03-14

Application number

SK1112-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Michael Sattlegger

Elke Reissm�Ller

Original Assignee

Grnenthal Gmbh

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.)

2001-03-14

Filing date

2002-03-13

Publication date

2004-01-08

2002-03-13 Application filed by Grnenthal Gmbh filed Critical Grnenthal Gmbh

2004-01-08 Publication of SK11122003A3 publication Critical patent/SK11122003A3/sk

Links

YDJWSFJCRATAJZ-UHFFFAOYSA-N n,n-dimethyl-1-[1-(1-phenylcyclohexyl)piperidin-3-yl]methanamine Chemical class C1C(CN(C)C)CCCN1C1(C=2C=CC=CC=2)CCCCC1 YDJWSFJCRATAJZ-UHFFFAOYSA-N 0.000 title claims abstract description 22
229940035676 analgesics Drugs 0.000 title description 3
239000000730 antalgic agent Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 58
239000003814 drug Substances 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims abstract description 6
208000002193 Pain Diseases 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
-1 methoxy, ethoxy, propoxy, butoxy Chemical group 0.000 claims description 14
230000036407 pain Effects 0.000 claims description 14
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
239000002585 base Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 claims description 4
239000007818 Grignard reagent Substances 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
150000002081 enamines Chemical class 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
150000004795 grignard reagents Chemical class 0.000 claims description 3
150000003840 hydrochlorides Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000005051 trimethylchlorosilane Substances 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
KAZYCBDNNBWEIO-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-1-(1-phenylcyclohexyl)-4-(2-phenylethyl)piperidin-4-ol Chemical compound CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)CCC1=CC=CC=C1 KAZYCBDNNBWEIO-UHFFFAOYSA-N 0.000 claims description 2
HOLHLWIBKJMWDG-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(2-fluorophenyl)-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)C1=CC=CC=C1F HOLHLWIBKJMWDG-UHFFFAOYSA-N 0.000 claims description 2
HBZYUAZHURKZQD-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(3-hydroxyphenyl)-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)C1=CC=CC(O)=C1 HBZYUAZHURKZQD-UHFFFAOYSA-N 0.000 claims description 2
MSABBFFJLCNOOB-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(3-methoxyphenyl)-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound COC1=CC=CC(C2(O)C(CN(CC2)C2(CCCCC2)C=2C=CC=CC=2)CN(C)C)=C1 MSABBFFJLCNOOB-UHFFFAOYSA-N 0.000 claims description 2
QUENHVLNQBKCOE-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-ethenyl-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound C1CC(C=C)(O)C(CN(C)C)CN1C1(C=2C=CC=CC=2)CCCCC1 QUENHVLNQBKCOE-UHFFFAOYSA-N 0.000 claims description 2
CKELZRQWLQBGNH-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-ethyl-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound C1C(CN(C)C)C(CC)(O)CCN1C1(C=2C=CC=CC=2)CCCCC1 CKELZRQWLQBGNH-UHFFFAOYSA-N 0.000 claims description 2
UNBAYYGMZSJUQL-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-octyl-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound C1C(CN(C)C)C(CCCCCCCC)(O)CCN1C1(C=2C=CC=CC=2)CCCCC1 UNBAYYGMZSJUQL-UHFFFAOYSA-N 0.000 claims description 2
LSJABBXCALAMFV-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-[(dimethylamino)methyl]-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)C1=CC=CC(Cl)=C1 LSJABBXCALAMFV-UHFFFAOYSA-N 0.000 claims description 2
KXKRZGPUFVQKOL-UHFFFAOYSA-N 4-benzyl-3-[(dimethylamino)methyl]-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)CC1=CC=CC=C1 KXKRZGPUFVQKOL-UHFFFAOYSA-N 0.000 claims description 2
JMDSPAUQLLZHRW-UHFFFAOYSA-N 4-butyl-3-[(dimethylamino)methyl]-1-(1-phenylcyclohexyl)piperidin-4-ol Chemical compound C1C(CN(C)C)C(CCCC)(O)CCN1C1(C=2C=CC=CC=2)CCCCC1 JMDSPAUQLLZHRW-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
235000013877 carbamide Nutrition 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
VVDUZZGYBOWDSQ-UHFFFAOYSA-M eschenmoser's salt Chemical compound [I-].C[N+](C)=C VVDUZZGYBOWDSQ-UHFFFAOYSA-M 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
150000003672 ureas Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
238000007796 conventional method Methods 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
229940124583 pain medication Drugs 0.000 claims 1
CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 claims 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 6
238000004519 manufacturing process Methods 0.000 abstract description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
125000005605 benzo group Chemical group 0.000 description 9
239000000243 solution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
239000012071 phase Substances 0.000 description 7
241000699670 Mus sp. Species 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
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 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
230000000202 analgesic effect Effects 0.000 description 5
238000003556 assay Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
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USSRQDDXGZPZGV-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-1-(1-phenylcyclohexyl)-4-(2-phenylethyl)piperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)CCC1=CC=CC=C1 USSRQDDXGZPZGV-UHFFFAOYSA-N 0.000 description 4
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230000000694 effects Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
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SMHROVDQOUWQQV-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(2-fluorophenyl)-1-(1-phenylcyclohexyl)piperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)C1=CC=CC=C1F SMHROVDQOUWQQV-UHFFFAOYSA-N 0.000 description 3
KSRLSDNIOGTESM-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(3-hydroxyphenyl)-1-(1-phenylcyclohexyl)piperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)C1=CC=CC(O)=C1 KSRLSDNIOGTESM-UHFFFAOYSA-N 0.000 description 3
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FFYMAAKSEORPOU-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-ethenyl-1-(1-phenylcyclohexyl)piperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(C=C)(O)C(CN(C)C)CN1C1(C=2C=CC=CC=2)CCCCC1 FFYMAAKSEORPOU-UHFFFAOYSA-N 0.000 description 3
CBBJPBBLZXMNBI-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-ethyl-1-(1-phenylcyclohexyl)piperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.C1C(CN(C)C)C(CC)(O)CCN1C1(C=2C=CC=CC=2)CCCCC1 CBBJPBBLZXMNBI-UHFFFAOYSA-N 0.000 description 3
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HHIABOOGPFRVIO-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-[(dimethylamino)methyl]-1-(1-phenylcyclohexyl)piperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1CN(C2(CCCCC2)C=2C=CC=CC=2)CCC1(O)C1=CC=CC(Cl)=C1 HHIABOOGPFRVIO-UHFFFAOYSA-N 0.000 description 3
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239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 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
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 1
FKUUDDGRDRPAQQ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C[C-]=C1 FKUUDDGRDRPAQQ-UHFFFAOYSA-M 0.000 description 1
HQDAZWQQKSJCTM-UHFFFAOYSA-M magnesium;octane;chloride Chemical compound [Mg+2].[Cl-].CCCCCCC[CH2-] HQDAZWQQKSJCTM-UHFFFAOYSA-M 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000008693 nausea Effects 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
230000002981 neuropathic effect Effects 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
239000000014 opioid analgesic Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000026416 response to pain Effects 0.000 description 1
230000036280 sedation Effects 0.000 description 1
230000020341 sensory perception of pain Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229960003107 tramadol hydrochloride Drugs 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
- 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
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK1112-2003A 2001-03-14 2002-03-13 Substituované dimetyl-[1-(1-fenyl-cyklohexyl)-piperidín-3- ylmetyl]-amíny, spôsob ich výroby, liečivá tieto látky obsahujúce a ich použitie SK11122003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10112198A DE10112198A1 (de)	2001-03-14	2001-03-14	Substituierte Dimethyl-[1-(1-phenyl-cyclohexyl)-piperidin-3-ylmethyl]-amine
PCT/EP2002/002723 WO2002072550A1 (de)	2001-03-14	2002-03-13	Substituierte dimethyl`1-(1-phenyl-cyclohexyl)-piperidin-3-ylmethyl!-amine und verwendung als analgetika

Publications (1)

Publication Number	Publication Date
SK11122003A3 true SK11122003A3 (sk)	2004-01-08

Family

ID=7677392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1112-2003A SK11122003A3 (sk)	2001-03-14	2002-03-13	Substituované dimetyl-[1-(1-fenyl-cyklohexyl)-piperidín-3- ylmetyl]-amíny, spôsob ich výroby, liečivá tieto látky obsahujúce a ich použitie

Country Status (23)

Country	Link
US (1)	US7049327B2 (cs)
EP (1)	EP1370529B1 (cs)
JP (1)	JP2004526726A (cs)
KR (1)	KR20040012733A (cs)
CN (1)	CN1496352A (cs)
AT (1)	ATE315551T1 (cs)
BR (1)	BR0208243A (cs)
CA (1)	CA2440758A1 (cs)
CZ (1)	CZ20032455A3 (cs)
DE (2)	DE10112198A1 (cs)
DK (1)	DK1370529T3 (cs)
EC (1)	ECSP034768A (cs)
ES (1)	ES2256499T3 (cs)
HU (1)	HUP0302800A2 (cs)
IL (1)	IL157893A0 (cs)
MX (1)	MXPA03007967A (cs)
NO (1)	NO20034029L (cs)
PE (1)	PE20020926A1 (cs)
PL (1)	PL364415A1 (cs)
RU (1)	RU2003129061A (cs)
SK (1)	SK11122003A3 (cs)
WO (1)	WO2002072550A1 (cs)
ZA (1)	ZA200307964B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105646332B (zh) *	2014-11-09	2018-05-25	复旦大学	氨基甲基哌啶类衍生物及其制备方法和药物用途
KR102603671B1 (ko) *	2017-01-17	2023-11-17	메비아스 디스커버리 인코포레이티드	치환된 3-디알킬아미노메틸-피페리딘-4-일-벤즈아미드 및 이를 제조 및 사용하는 방법

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL40064A0 (en) *	1972-08-07	1972-10-29	Univ Tel Aviv	Phencyclidine and its derivatives as short-time acting midriatics
WO1998055478A1 (fr) *	1997-06-03	1998-12-10	Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.)	Nouveaux derives de phencyclidines, des procedes pour leur preparation et des compositions pharmaceutiques les contenant
US4598153A (en) *	1984-12-19	1986-07-01	The United States Of America As Represented By The Department Of Health And Human Services	Metaphit, a specific acylating agent for the [3 H] phencyclidine
US5155212A (en) *	1986-05-21	1992-10-13	Abbott Laboratories	Phencyclidine and phencyclidine metabolites assay, tracers, immunogens, antibodies and reagent kit
HUT77318A (hu) *	1994-09-30	1998-03-30	Novartis Ag.	1-Acil-4-/(alifás amino)-piperidin/-származékok, e vegyületeket tartalmazó gyógyszerkészítmények, eljárás előállításukra és alkalmazásuk
ID29137A (id) *	1998-07-27	2001-08-02	Schering Corp	Ligan-ligan afinitas tinggi untuk reseptor nosiseptin orl-1
DE10000312A1 (de) *	2000-01-05	2001-07-12	Gruenenthal Gmbh	Substituierte Aminomethyl-Phenyl-Cyclohexanderivate

2001
- 2001-03-14 DE DE10112198A patent/DE10112198A1/de not_active Withdrawn
2002
- 2002-03-13 MX MXPA03007967A patent/MXPA03007967A/es not_active Application Discontinuation
- 2002-03-13 PL PL02364415A patent/PL364415A1/xx unknown
- 2002-03-13 PE PE2002000199A patent/PE20020926A1/es not_active Application Discontinuation
- 2002-03-13 EP EP02750542A patent/EP1370529B1/de not_active Expired - Lifetime
- 2002-03-13 WO PCT/EP2002/002723 patent/WO2002072550A1/de not_active Ceased
- 2002-03-13 SK SK1112-2003A patent/SK11122003A3/sk unknown
- 2002-03-13 RU RU2003129061/04A patent/RU2003129061A/ru not_active Application Discontinuation
- 2002-03-13 DK DK02750542T patent/DK1370529T3/da active
- 2002-03-13 AT AT02750542T patent/ATE315551T1/de active
- 2002-03-13 IL IL15789302A patent/IL157893A0/xx unknown
- 2002-03-13 CZ CZ20032455A patent/CZ20032455A3/cs unknown
- 2002-03-13 DE DE50205593T patent/DE50205593D1/de not_active Expired - Lifetime
- 2002-03-13 CN CNA028064135A patent/CN1496352A/zh active Pending
- 2002-03-13 CA CA002440758A patent/CA2440758A1/en not_active Abandoned
- 2002-03-13 HU HU0302800A patent/HUP0302800A2/hu unknown
- 2002-03-13 KR KR10-2003-7011908A patent/KR20040012733A/ko not_active Withdrawn
- 2002-03-13 BR BR0208243-8A patent/BR0208243A/pt not_active Application Discontinuation
- 2002-03-13 ES ES02750542T patent/ES2256499T3/es not_active Expired - Lifetime
- 2002-03-13 JP JP2002571466A patent/JP2004526726A/ja not_active Withdrawn
2003
- 2003-09-11 NO NO20034029A patent/NO20034029L/no not_active Application Discontinuation
- 2003-09-12 EC EC2003004768A patent/ECSP034768A/es unknown
- 2003-09-12 US US10/660,729 patent/US7049327B2/en not_active Expired - Fee Related
- 2003-10-13 ZA ZA200307964A patent/ZA200307964B/en unknown

Also Published As

Publication number	Publication date
ATE315551T1 (de)	2006-02-15
NO20034029D0 (no)	2003-09-11
CZ20032455A3 (cs)	2003-12-17
KR20040012733A (ko)	2004-02-11
PE20020926A1 (es)	2002-10-26
ES2256499T3 (es)	2006-07-16
MXPA03007967A (es)	2004-10-15
RU2003129061A (ru)	2005-04-10
JP2004526726A (ja)	2004-09-02
PL364415A1 (en)	2004-12-13
US20040127516A1 (en)	2004-07-01
DE50205593D1 (de)	2006-04-06
DE10112198A1 (de)	2002-09-19
CN1496352A (zh)	2004-05-12
NO20034029L (no)	2003-11-13
HUP0302800A2 (hu)	2003-11-28
EP1370529B1 (de)	2006-01-11
IL157893A0 (en)	2004-03-28
ZA200307964B (en)	2004-09-14
DK1370529T3 (da)	2006-05-22
EP1370529A1 (de)	2003-12-17
US7049327B2 (en)	2006-05-23
CA2440758A1 (en)	2002-09-19
ECSP034768A (es)	2003-10-28
BR0208243A (pt)	2004-03-09
WO2002072550A1 (de)	2002-09-19

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US7326722B2 (en)	2008-02-05	N-[Phenyl(piperidin-2-yl)methyl]benzamide derivatives, their preparation and their application in therapy
US7951821B2 (en)	2011-05-31	N-[phenyl(piperidin-2-yl)methyl]benzamide derivatives, preparation thereof, and use thereof in therapy
RU2351588C2 (ru)	2009-04-10	Производные n-фенил(пиперидин-2-ил)метил-бензамида и их применение в терапии
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AU2001275326B2 (en)	2006-02-02	Treatment of gastroesophageal reflux disease using piperidine derivatives
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US20080070898A1 (en)	2008-03-20	Piperidine Derivative or Pharmaceutically Acceptable Salt Thereof
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