ES2231304T3 - Derivados de aminometil fenil ciclohexanona. - Google Patents
Derivados de aminometil fenil ciclohexanona.Info
- Publication number
- ES2231304T3 ES2231304T3 ES00990824T ES00990824T ES2231304T3 ES 2231304 T3 ES2231304 T3 ES 2231304T3 ES 00990824 T ES00990824 T ES 00990824T ES 00990824 T ES00990824 T ES 00990824T ES 2231304 T3 ES2231304 T3 ES 2231304T3
- Authority
- ES
- Spain
- Prior art keywords
- carbons
- substituted
- unsubstituted
- alkyl
- dimethylaminomethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 167
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 139
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 111
- 150000001721 carbon Chemical group 0.000 claims abstract description 111
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 99
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 99
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 61
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 61
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 54
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 53
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 44
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 37
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 35
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 35
- NWSCVDPHHGDSBE-UHFFFAOYSA-N 2-(aminomethyl)-2-phenylcyclohexan-1-one Chemical class C=1C=CC=CC=1C1(CN)CCCCC1=O NWSCVDPHHGDSBE-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 150000007513 acids Chemical class 0.000 claims abstract description 16
- 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 abstract description 9
- 150000003840 hydrochlorides Chemical class 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 22
- -1 salts hydrochloride Chemical class 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- UFXPDNGKMSEVHV-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound CN(C)CC1CCC(=O)CC1C1=CC=CC(O)=C1 UFXPDNGKMSEVHV-UHFFFAOYSA-N 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 208000002193 Pain Diseases 0.000 claims description 13
- 230000036407 pain Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- QRQZXONDVGVNQH-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohex-2-en-1-one Chemical compound COC1=CC=CC(C=2C(CCC(=O)C=2)CN(C)C)=C1 QRQZXONDVGVNQH-UHFFFAOYSA-N 0.000 claims description 7
- PKXKHMUMACVYHM-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-hydroxy-3-(3-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=CC(C2(O)C(CCC(=O)C2)CN(C)C)=C1 PKXKHMUMACVYHM-UHFFFAOYSA-N 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- BFQUXINHKGBHLT-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-4-[(dimethylamino)methyl]cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=C(F)C(F)=C1 BFQUXINHKGBHLT-UHFFFAOYSA-N 0.000 claims description 5
- IANBCHYJKGEOEV-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-4-[(dimethylamino)methyl]cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC(Cl)=CC(Cl)=C1 IANBCHYJKGEOEV-UHFFFAOYSA-N 0.000 claims description 5
- BAPSMKYJGSSKKI-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-4-[(dimethylamino)methyl]cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC(F)=CC(F)=C1 BAPSMKYJGSSKKI-UHFFFAOYSA-N 0.000 claims description 5
- KQKZQCQYVBWYHB-UHFFFAOYSA-N 3-[3-(difluoromethyl)phenyl]-4-[(dimethylamino)methyl]cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=CC(C(F)F)=C1 KQKZQCQYVBWYHB-UHFFFAOYSA-N 0.000 claims description 5
- NCZWDXKBNIMFQP-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(3-fluorophenyl)cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=CC(F)=C1 NCZWDXKBNIMFQP-UHFFFAOYSA-N 0.000 claims description 5
- FQUDADXUSNUPMC-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(3-hydroxyphenyl)cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=CC(O)=C1 FQUDADXUSNUPMC-UHFFFAOYSA-N 0.000 claims description 5
- RUBAZYTVFGSKSK-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(4-fluorophenyl)cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=C(F)C=C1 RUBAZYTVFGSKSK-UHFFFAOYSA-N 0.000 claims description 5
- UJAURWYSPLJUMU-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(4-methoxyphenyl)cyclohex-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)CCC1CN(C)C UJAURWYSPLJUMU-UHFFFAOYSA-N 0.000 claims description 5
- KMCQGZMJLRZRSV-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(6-methoxynaphthalen-2-yl)cyclohex-2-en-1-one Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1=CC(=O)CCC1CN(C)C KMCQGZMJLRZRSV-UHFFFAOYSA-N 0.000 claims description 5
- HNWYHTFBGUFONL-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-[4-(trifluoromethyl)phenyl]cyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=C(C(F)(F)F)C=C1 HNWYHTFBGUFONL-UHFFFAOYSA-N 0.000 claims description 5
- QSYOGYPHPHSUMF-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-naphthalen-2-ylcyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=C(C=CC=C2)C2=C1 QSYOGYPHPHSUMF-UHFFFAOYSA-N 0.000 claims description 5
- SKCVIWLQHBSPFI-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-phenylcyclohex-2-en-1-one Chemical compound CN(C)CC1CCC(=O)C=C1C1=CC=CC=C1 SKCVIWLQHBSPFI-UHFFFAOYSA-N 0.000 claims description 5
- SROFOCUMLZWZIM-WFASDCNBSA-N CN(C)C[C@@H]1CCC(=O)C[C@H]1C1=CC=CC(F)=C1 Chemical compound CN(C)C[C@@H]1CCC(=O)C[C@H]1C1=CC=CC(F)=C1 SROFOCUMLZWZIM-WFASDCNBSA-N 0.000 claims description 5
- GBJBAKOEQBLBPL-ZFWWWQNUSA-N CN(C)C[C@@H]1CCC(=O)C[C@H]1C1=CC=CC=C1 Chemical compound CN(C)C[C@@H]1CCC(=O)C[C@H]1C1=CC=CC=C1 GBJBAKOEQBLBPL-ZFWWWQNUSA-N 0.000 claims description 5
- SROFOCUMLZWZIM-DOMZBBRYSA-N CN(C)C[C@H]1CCC(=O)C[C@H]1C1=CC=CC(F)=C1 Chemical compound CN(C)C[C@H]1CCC(=O)C[C@H]1C1=CC=CC(F)=C1 SROFOCUMLZWZIM-DOMZBBRYSA-N 0.000 claims description 5
- GBJBAKOEQBLBPL-HIFRSBDPSA-N CN(C)C[C@H]1CCC(=O)C[C@H]1C1=CC=CC=C1 Chemical compound CN(C)C[C@H]1CCC(=O)C[C@H]1C1=CC=CC=C1 GBJBAKOEQBLBPL-HIFRSBDPSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 5
- HJPSHWFGNDBKHV-BBRMVZONSA-N (3R,4R)-4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=CC([C@H]2[C@@H](CCC(=O)C2)CN(C)C)=C1 HJPSHWFGNDBKHV-BBRMVZONSA-N 0.000 claims description 4
- HJPSHWFGNDBKHV-CJNGLKHVSA-N (3R,4S)-4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=CC([C@H]2[C@H](CCC(=O)C2)CN(C)C)=C1 HJPSHWFGNDBKHV-CJNGLKHVSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000012467 final product Substances 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 208000003251 Pruritus Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 206010011224 Cough Diseases 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- 208000007882 Gastritis Diseases 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 206010001584 alcohol abuse Diseases 0.000 claims description 2
- 208000025746 alcohol use disease Diseases 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 230000003236 psychic effect Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000012458 free base Substances 0.000 claims 2
- QIFSGRPJUXQGMD-UHFFFAOYSA-N 3,3-dimethyl-1,5-dioxaspiro[5.5]undecane Chemical compound O1CC(C)(C)COC11CCCCC1 QIFSGRPJUXQGMD-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 235000002639 sodium chloride Nutrition 0.000 description 16
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000014509 gene expression Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000005051 trimethylchlorosilane Substances 0.000 description 7
- BXCBHDJKDXLFAF-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohex-2-en-1-one;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C(CCC(=O)C=2)CN(C)C)=C1 BXCBHDJKDXLFAF-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002483 medication Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
- GBJPHWSARPWFGF-UHFFFAOYSA-N 9-[(dimethylamino)methyl]-1,5-dioxaspiro[5.5]undecan-10-one Chemical compound C1C(=O)C(CN(C)C)CCC21OCCCO2 GBJPHWSARPWFGF-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- NHFVEBWIBVLQKP-UHFFFAOYSA-N 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-10-one Chemical compound O1CC(C)(C)COC11CC(=O)CCC1 NHFVEBWIBVLQKP-UHFFFAOYSA-N 0.000 description 3
- LVHXNNHYTOYSOE-UHFFFAOYSA-N 9-[(dimethylamino)methyl]-10-(3-methoxyphenyl)-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-10-ol Chemical compound COC1=CC=CC(C2(O)C(CCC3(C2)OCC(C)(C)CO3)CN(C)C)=C1 LVHXNNHYTOYSOE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 125000004432 carbon atom Chemical group C* 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
- 239000003480 eluent Substances 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
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Classifications
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- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C225/18—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings the carbon skeleton containing also rings other than six-membered aromatic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/12—Antidiarrhoeals
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10000311 | 2000-01-05 | ||
| DE10000311A DE10000311A1 (de) | 2000-01-05 | 2000-01-05 | Aminomethyl-Phonyl-Cyclohexanonderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2231304T3 true ES2231304T3 (es) | 2005-05-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00990824T Expired - Lifetime ES2231304T3 (es) | 2000-01-05 | 2000-12-27 | Derivados de aminometil fenil ciclohexanona. |
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| EP (1) | EP1246791B1 (enExample) |
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7457762B2 (en) * | 2001-09-04 | 2008-11-25 | Accenture Global Services Gmbh | Optimization of management of maintenance, repair and overhaul of equipment in a specified time window |
| DE10326097A1 (de) * | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
| DE10328316A1 (de) | 2003-06-23 | 2005-01-20 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| US7260408B2 (en) * | 2004-02-20 | 2007-08-21 | Airespace, Inc. | Wireless node location mechanism using antenna pattern diversity to enhance accuracy of location estimates |
| US20050236892A1 (en) * | 2004-04-27 | 2005-10-27 | Akihito Kusano | Hydraulic braking pressure generating apparatus for vehicles |
| DE102005052588A1 (de) | 2005-11-02 | 2007-05-10 | Grünenthal GmbH | Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse |
| TWI448447B (zh) | 2006-07-24 | 2014-08-11 | Gruenenthal Chemie | 製備（１ｒ，２ｒ）-３-（３-二甲胺基-１-乙基-２-甲基-丙基）-酚之方法 |
| JP5009736B2 (ja) * | 2007-10-15 | 2012-08-22 | 日本曹達株式会社 | 環状アミノエーテルを用いたマンニッヒ反応 |
| EP2262759A1 (de) * | 2008-02-29 | 2010-12-22 | Grünenthal GmbH | Verfahren zur herstellung von (1rs,3rs,6rs)-6-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexan-1,3-diol |
Family Cites Families (11)
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| DE1518663A1 (de) * | 1965-08-02 | 1969-12-18 | Gruenenthal Chemie | Basisch substituierte Cycloalken-derivate und Verfahren zu ihrer Herstellung |
| US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
| US3974157A (en) * | 1974-03-04 | 1976-08-10 | Pennwalt Corporation | 1-(Amino-alkyl)-2-aryl-cyclohexane alcohols and esters |
| JPS51143650A (en) * | 1975-06-06 | 1976-12-10 | Takeda Chem Ind Ltd | A process for preparing cyclohexanol derivatives |
| ATE147732T1 (de) | 1989-03-08 | 1997-02-15 | Merck Sharp & Dohme | Tetrahydroquinolin-derivate, verwendbar bei neurodegenerativen krankheiten |
| IL112569A (en) * | 1994-02-10 | 1999-12-22 | Wyeth John & Brother Ltd | Pharmaceutical compositions comprising cyclohexylamine derivatives certain such novel compounds and their preparation |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19547766A1 (de) * | 1995-12-20 | 1997-06-26 | Gruenenthal Gmbh | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
| DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| MY125037A (en) | 1998-06-10 | 2006-07-31 | Glaxo Wellcome Spa | 1,2,3,4 tetrahydroquinoline derivatives |
| DE19830105C1 (de) * | 1998-07-06 | 2000-02-17 | Gruenenthal Gmbh | Acridinderivate |
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2000
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- 2000-12-27 CN CNB008192669A patent/CN100467441C/zh not_active Expired - Fee Related
- 2000-12-27 PL PL00356642A patent/PL356642A1/xx unknown
- 2000-12-27 IL IL15055800A patent/IL150558A0/xx active IP Right Grant
- 2000-12-27 JP JP2001550191A patent/JP2003519209A/ja active Pending
- 2000-12-27 KR KR1020027008706A patent/KR100748378B1/ko not_active Expired - Fee Related
- 2000-12-27 RU RU2002120897/04A patent/RU2002120897A/ru unknown
- 2000-12-27 CA CA002396310A patent/CA2396310A1/en not_active Abandoned
- 2000-12-27 HU HU0203859A patent/HUP0203859A3/hu unknown
- 2000-12-27 SI SI200030587T patent/SI1246791T1/xx unknown
- 2000-12-27 WO PCT/EP2000/013282 patent/WO2001049651A2/de not_active Ceased
- 2000-12-27 MX MXPA02006697A patent/MXPA02006697A/es active IP Right Grant
- 2000-12-27 DK DK00990824T patent/DK1246791T3/da active
- 2000-12-27 AT AT00990824T patent/ATE280752T1/de active
- 2000-12-27 SK SK980-2002A patent/SK286799B6/sk not_active IP Right Cessation
- 2000-12-27 PT PT00990824T patent/PT1246791E/pt unknown
- 2000-12-27 AU AU30169/01A patent/AU782862B2/en not_active Ceased
- 2000-12-27 BR BR0016941-2A patent/BR0016941A/pt not_active Application Discontinuation
- 2000-12-27 NZ NZ520468A patent/NZ520468A/en unknown
- 2000-12-27 ES ES00990824T patent/ES2231304T3/es not_active Expired - Lifetime
- 2000-12-27 CZ CZ20022338A patent/CZ20022338A3/cs unknown
- 2000-12-27 DE DE50008447T patent/DE50008447D1/de not_active Expired - Lifetime
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2001
- 2001-01-02 AR ARP010100008A patent/AR030683A1/es unknown
- 2001-01-04 CO CO01000529A patent/CO5261627A1/es not_active Application Discontinuation
- 2001-01-04 PE PE2001000012A patent/PE20011043A1/es not_active Application Discontinuation
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2002
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- 2002-07-03 IL IL150558A patent/IL150558A/en not_active IP Right Cessation
- 2002-07-05 US US10/189,184 patent/US6890959B2/en not_active Expired - Fee Related
- 2002-08-01 ZA ZA200206150A patent/ZA200206150B/xx unknown
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