DE2749214A1 - N-(2-aminocyclopentyl)-n-alkanoylanilide oder deren 2-n-oxide, verfahren zu ihrer herstellung und verwendung derselben bei der behandlung depressiver zustaende - Google Patents
N-(2-aminocyclopentyl)-n-alkanoylanilide oder deren 2-n-oxide, verfahren zu ihrer herstellung und verwendung derselben bei der behandlung depressiver zustaendeInfo
- Publication number
- DE2749214A1 DE2749214A1 DE19772749214 DE2749214A DE2749214A1 DE 2749214 A1 DE2749214 A1 DE 2749214A1 DE 19772749214 DE19772749214 DE 19772749214 DE 2749214 A DE2749214 A DE 2749214A DE 2749214 A1 DE2749214 A1 DE 2749214A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- pharmacologically acceptable
- propionanilide
- dichloro
- acceptable salts
- 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.)
- Granted
Links
- -1 2-AMINOCYCLOPENTYL Chemical class 0.000 title claims description 71
- 238000000034 method Methods 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 28
- 230000003001 depressive effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 114
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 113
- 150000003839 salts Chemical class 0.000 claims description 89
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 claims description 60
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 27
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000935 antidepressant agent Substances 0.000 claims description 15
- 229940005513 antidepressants Drugs 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 150000004985 diamines Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 11
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 230000001430 anti-depressive effect Effects 0.000 claims description 9
- 208000020401 Depressive disease Diseases 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims description 6
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- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- AZTGEJBZSFKULT-UHFFFAOYSA-N n-phenylcyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NC1=CC=CC=C1 AZTGEJBZSFKULT-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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- 231100000252 nontoxic Toxicity 0.000 claims description 2
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- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- MKSDKVCAQYBVFW-UHFFFAOYSA-N 3,4-dichloro-n-[2-(dimethylamino)cyclopentyl]-n-phenylbutanamide Chemical compound CN(C)C1CCCC1N(C(=O)CC(Cl)CCl)C1=CC=CC=C1 MKSDKVCAQYBVFW-UHFFFAOYSA-N 0.000 claims 1
- GBBBTEAKVWMXIL-UHFFFAOYSA-N 3-bromo-n-[4-bromo-2-(dimethylamino)cyclopentyl]-n-phenylpropanamide Chemical compound CN(C)C1CC(Br)CC1N(C(=O)CCBr)C1=CC=CC=C1 GBBBTEAKVWMXIL-UHFFFAOYSA-N 0.000 claims 1
- UQMKXMVFCHRTQJ-UHFFFAOYSA-N 3-chloro-n-(4-chloro-2-pyrrolidin-1-ylcyclopentyl)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCCl)C1CC(Cl)CC1N1CCCC1 UQMKXMVFCHRTQJ-UHFFFAOYSA-N 0.000 claims 1
- KSLMJRXPBMCRNO-UHFFFAOYSA-N 3-chloro-n-[2-(dimethylamino)-4-fluorocyclopentyl]-n-phenylpropanamide Chemical compound CN(C)C1CC(F)CC1N(C(=O)CCCl)C1=CC=CC=C1 KSLMJRXPBMCRNO-UHFFFAOYSA-N 0.000 claims 1
- YMYYMHWILPOKIJ-UHFFFAOYSA-N 3-chloro-n-[2-(dimethylamino)-4-methylcyclopentyl]-n-phenylpropanamide Chemical compound C1C(C)CC(N(C)C)C1N(C(=O)CCCl)C1=CC=CC=C1 YMYYMHWILPOKIJ-UHFFFAOYSA-N 0.000 claims 1
- UDMDYILGZPRTDJ-UHFFFAOYSA-N 3-chloro-n-[2-(dimethylamino)cyclopentyl]-n-phenylpropanamide Chemical compound CN(C)C1CCCC1N(C(=O)CCCl)C1=CC=CC=C1 UDMDYILGZPRTDJ-UHFFFAOYSA-N 0.000 claims 1
- RIKHZLPQXNQLRH-UHFFFAOYSA-N 3-chloro-n-[2-chloro-5-(dimethylamino)cyclopentyl]-n-phenylpropanamide Chemical compound CN(C)C1CCC(Cl)C1N(C(=O)CCCl)C1=CC=CC=C1 RIKHZLPQXNQLRH-UHFFFAOYSA-N 0.000 claims 1
- MDXSQZWFKCPMAP-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-(diethylamino)cyclopentyl]-n-phenylpropanamide Chemical compound CCN(CC)C1CC(Cl)CC1N(C(=O)CCCl)C1=CC=CC=C1 MDXSQZWFKCPMAP-UHFFFAOYSA-N 0.000 claims 1
- QEPLZHWIEBBHBC-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-(dimethylamino)cyclopentyl]-n-phenylpropanethioamide Chemical compound CN(C)C1CC(Cl)CC1N(C(=S)CCCl)C1=CC=CC=C1 QEPLZHWIEBBHBC-UHFFFAOYSA-N 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- WYJQQGCESZFRLI-UHFFFAOYSA-N n-[2-(dimethylamino)-4-methylcyclopentyl]-n-phenylbutanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCC)C1CC(C)CC1N(C)C WYJQQGCESZFRLI-UHFFFAOYSA-N 0.000 claims 1
- HKQCUOQHKNGOLF-UHFFFAOYSA-N n-[2-(dimethylamino)cyclopentyl]-3-fluoro-n-phenylpropanamide Chemical compound CN(C)C1CCCC1N(C(=O)CCF)C1=CC=CC=C1 HKQCUOQHKNGOLF-UHFFFAOYSA-N 0.000 claims 1
- KSLVOVWRLBGIAX-UHFFFAOYSA-N n-[2-(dimethylamino)cyclopentyl]-3-methoxy-n-phenylpropanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCOC)C1CCCC1N(C)C KSLVOVWRLBGIAX-UHFFFAOYSA-N 0.000 claims 1
- WXUYDVKXRRSZAF-UHFFFAOYSA-N n-[2-(dimethylamino)cyclopentyl]-n-phenylbutanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCC)C1CCCC1N(C)C WXUYDVKXRRSZAF-UHFFFAOYSA-N 0.000 claims 1
- LIURIAAYXSHINV-UHFFFAOYSA-N n-[4-bromo-2-(dimethylamino)cyclopentyl]-n-phenylpropanamide Chemical compound C=1C=CC=CC=1N(C(=O)CC)C1CC(Br)CC1N(C)C LIURIAAYXSHINV-UHFFFAOYSA-N 0.000 claims 1
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- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229960002861 doxepin hydrochloride Drugs 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N para-methoxybenzyl alcohol Natural products COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification 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
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000052 vinegar Chemical class 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74619176A | 1976-11-30 | 1976-11-30 | |
| US77759977A | 1977-03-15 | 1977-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2749214A1 true DE2749214A1 (de) | 1978-06-01 |
| DE2749214C2 DE2749214C2 (enrdf_load_stackoverflow) | 1987-11-05 |
Family
ID=27114572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772749214 Granted DE2749214A1 (de) | 1976-11-30 | 1977-11-03 | N-(2-aminocyclopentyl)-n-alkanoylanilide oder deren 2-n-oxide, verfahren zu ihrer herstellung und verwendung derselben bei der behandlung depressiver zustaende |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5368748A (enrdf_load_stackoverflow) |
| AU (1) | AU511200B2 (enrdf_load_stackoverflow) |
| CH (1) | CH636340A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2749214A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2384495A1 (enrdf_load_stackoverflow) |
| GB (2) | GB1560219A (enrdf_load_stackoverflow) |
| NL (1) | NL7712899A (enrdf_load_stackoverflow) |
| SE (1) | SE441444B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7803442A (nl) * | 1978-02-09 | 1979-08-13 | Upjohn Co | Werkwijzen voor het bereiden en toepassen van amino-cycloalifatische amiden. |
| IE58999B1 (en) * | 1985-07-22 | 1993-12-15 | Rolland Sa A | Novel N-oxyde of NN-dimethyl ethylamine, a process for it's production and the pharmaceutical compositions containing it |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510492A (en) * | 1968-05-13 | 1970-05-05 | Upjohn Co | 2-anilino and 2-anilinomethyl cycloalkylamines |
-
1977
- 1977-11-03 DE DE19772749214 patent/DE2749214A1/de active Granted
- 1977-11-09 AU AU30489/77A patent/AU511200B2/en not_active Expired
- 1977-11-10 GB GB46747/78A patent/GB1560219A/en not_active Expired
- 1977-11-10 GB GB46750/77A patent/GB1560218A/en not_active Expired
- 1977-11-23 NL NL7712899A patent/NL7712899A/xx not_active Application Discontinuation
- 1977-11-28 SE SE7713439A patent/SE441444B/xx not_active IP Right Cessation
- 1977-11-28 JP JP14258077A patent/JPS5368748A/ja active Pending
- 1977-11-29 FR FR7735909A patent/FR2384495A1/fr active Granted
- 1977-11-29 CH CH1461277A patent/CH636340A5/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510492A (en) * | 1968-05-13 | 1970-05-05 | Upjohn Co | 2-anilino and 2-anilinomethyl cycloalkylamines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2384495A1 (fr) | 1978-10-20 |
| FR2384495B1 (enrdf_load_stackoverflow) | 1980-07-25 |
| JPS5368748A (en) | 1978-06-19 |
| DE2749214C2 (enrdf_load_stackoverflow) | 1987-11-05 |
| GB1560218A (en) | 1980-01-30 |
| SE441444B (sv) | 1985-10-07 |
| SE7713439L (sv) | 1978-05-31 |
| NL7712899A (nl) | 1978-06-01 |
| AU511200B2 (en) | 1980-07-31 |
| AU3048977A (en) | 1979-05-17 |
| GB1560219A (en) | 1980-01-30 |
| CH636340A5 (en) | 1983-05-31 |
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