DE2227842C3 - Diphenylcyclopentane und diese enthaltende Arzneimittel - Google Patents
Diphenylcyclopentane und diese enthaltende ArzneimittelInfo
- Publication number
- DE2227842C3 DE2227842C3 DE19722227842 DE2227842A DE2227842C3 DE 2227842 C3 DE2227842 C3 DE 2227842C3 DE 19722227842 DE19722227842 DE 19722227842 DE 2227842 A DE2227842 A DE 2227842A DE 2227842 C3 DE2227842 C3 DE 2227842C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- diphenylcyclopentane
- uptake
- hydrochloride
- hours
- 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
Links
- BMIAZROFYUGBEL-UHFFFAOYSA-N (1-phenylcyclopentyl)benzene Chemical compound C1CCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 BMIAZROFYUGBEL-UHFFFAOYSA-N 0.000 title claims description 5
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 15
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- 229960004801 imipramine Drugs 0.000 description 12
- MOWLUBGHVYJYTK-UHFFFAOYSA-N 3-(2-aminoethyl)indol-3-ol Chemical compound C1=CC=C2C(CCN)(O)C=NC2=C1 MOWLUBGHVYJYTK-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
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- 230000005764 inhibitory process Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical group C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
- KNNJWHYARPPXGD-UHFFFAOYSA-N 3,3-diphenylcyclopentan-1-amine;hydrochloride Chemical compound Cl.C1C(N)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 KNNJWHYARPPXGD-UHFFFAOYSA-N 0.000 description 5
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- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 5
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- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- YTQSRKGRMBCRCH-UHFFFAOYSA-N (3,3-diphenylcyclopentyl)methanamine;hydrochloride Chemical compound Cl.C1C(CN)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 YTQSRKGRMBCRCH-UHFFFAOYSA-N 0.000 description 3
- PQHVRLNMNDNONP-UHFFFAOYSA-N 1-(3,3-diphenylcyclopentyl)-n-methylmethanamine;hydrochloride Chemical compound Cl.C1C(CNC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 PQHVRLNMNDNONP-UHFFFAOYSA-N 0.000 description 3
- SSLWPEGXWRKAAA-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-phenylcyclopentan-1-amine;hydrochloride Chemical compound Cl.C1C(N)CCC1(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 SSLWPEGXWRKAAA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- 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 3
- -1 Lithium aluminum hydride Chemical compound 0.000 description 3
- 102000010909 Monoamine Oxidase Human genes 0.000 description 3
- 108010062431 Monoamine oxidase Proteins 0.000 description 3
- 208000006550 Mydriasis Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010035039 Piloerection Diseases 0.000 description 3
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 206010046996 Varicose vein Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
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- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
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- 239000001257 hydrogen Substances 0.000 description 3
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- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
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- 239000003029 tricyclic antidepressant agent Substances 0.000 description 3
- HYQSULXEQVUVML-UHFFFAOYSA-N 1-(3,3-diphenylcyclopentyl)-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.C1C(CN(C)C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 HYQSULXEQVUVML-UHFFFAOYSA-N 0.000 description 2
- IBKPGNYXUIJNEK-UHFFFAOYSA-N 3,3-bis(4-chlorophenyl)cyclopentan-1-amine;hydrochloride Chemical compound Cl.C1C(N)CCC1(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IBKPGNYXUIJNEK-UHFFFAOYSA-N 0.000 description 2
- PNZFHLCSGMLZIB-UHFFFAOYSA-N 3,3-diphenylcyclopentan-1-one Chemical compound C1C(=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 PNZFHLCSGMLZIB-UHFFFAOYSA-N 0.000 description 2
- KAEXOMUNHHLZCE-UHFFFAOYSA-N 3-(4-chlorophenyl)-n,n-dimethyl-3-phenylcyclopentan-1-amine;hydrochloride Chemical compound Cl.C1C(N(C)C)CCC1(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 KAEXOMUNHHLZCE-UHFFFAOYSA-N 0.000 description 2
- MVVAEAUAWZPBFQ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-phenylcyclopentan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(C=2C=CC=CC=2)CC(N)CC1 MVVAEAUAWZPBFQ-UHFFFAOYSA-N 0.000 description 2
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 229920002261 Corn starch Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- 239000012839 Krebs-Henseleit buffer Substances 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- 208000007623 Lordosis Diseases 0.000 description 1
- 206010028347 Muscle twitching Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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- 229940124639 Selective inhibitor Drugs 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
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- 125000002015 acyclic group Chemical group 0.000 description 1
- 210000002934 adrenergic neuron Anatomy 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960002795 dl- norepinephrine Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 230000001730 monoaminergic effect Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- BCBIDXOBWXECET-UHFFFAOYSA-N n,n-dimethyl-3,3-diphenylcyclopentan-1-amine;hydrochloride Chemical compound Cl.C1C(N(C)C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 BCBIDXOBWXECET-UHFFFAOYSA-N 0.000 description 1
- 230000007383 nerve stimulation Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000012154 norepinephrine uptake Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- MILWSGRFEGYSGM-UHFFFAOYSA-N propane-1,2-diol;propane-1,2,3-triol Chemical compound CC(O)CO.OCC(O)CO MILWSGRFEGYSGM-UHFFFAOYSA-N 0.000 description 1
- 230000037047 psychomotor activity Effects 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000001179 pupillary effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE763171A SE376413B (enExample) | 1971-06-11 | 1971-06-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2227842A1 DE2227842A1 (de) | 1972-12-21 |
| DE2227842B2 DE2227842B2 (de) | 1975-03-27 |
| DE2227842C3 true DE2227842C3 (de) | 1975-11-27 |
Family
ID=20271885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722227842 Expired DE2227842C3 (de) | 1971-06-11 | 1972-06-08 | Diphenylcyclopentane und diese enthaltende Arzneimittel |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS525498B1 (enExample) |
| AT (1) | AT324317B (enExample) |
| AU (1) | AU471250B2 (enExample) |
| BE (2) | BE784719A (enExample) |
| CA (1) | CA1005075A (enExample) |
| CH (4) | CH587219A5 (enExample) |
| DE (1) | DE2227842C3 (enExample) |
| DK (1) | DK136243B (enExample) |
| FR (1) | FR2140662B1 (enExample) |
| GB (1) | GB1372644A (enExample) |
| NL (1) | NL7208008A (enExample) |
| NO (1) | NO133972C (enExample) |
| SE (1) | SE376413B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5642232U (enExample) * | 1979-09-10 | 1981-04-17 |
-
1971
- 1971-06-11 SE SE763171A patent/SE376413B/xx unknown
-
1972
- 1972-06-05 CA CA143,852A patent/CA1005075A/en not_active Expired
- 1972-06-07 AU AU43176/72A patent/AU471250B2/en not_active Expired
- 1972-06-07 AT AT487672A patent/AT324317B/de not_active IP Right Cessation
- 1972-06-08 DE DE19722227842 patent/DE2227842C3/de not_active Expired
- 1972-06-09 CH CH1452776A patent/CH587219A5/xx not_active IP Right Cessation
- 1972-06-09 FR FR7220948A patent/FR2140662B1/fr not_active Expired
- 1972-06-09 CH CH862572A patent/CH577457A5/xx not_active IP Right Cessation
- 1972-06-09 GB GB2708172A patent/GB1372644A/en not_active Expired
- 1972-06-09 CH CH545276A patent/CH586652A5/xx not_active IP Right Cessation
- 1972-06-09 CH CH1452676A patent/CH587218A5/xx not_active IP Right Cessation
- 1972-06-09 NO NO204972A patent/NO133972C/no unknown
- 1972-06-09 DK DK288472A patent/DK136243B/da unknown
- 1972-06-10 JP JP5813972A patent/JPS525498B1/ja active Pending
- 1972-06-12 BE BE784719A patent/BE784719A/xx unknown
- 1972-06-12 NL NL7208008A patent/NL7208008A/xx not_active Application Discontinuation
- 1972-06-12 BE BE784718A patent/BE784718A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK136243C (enExample) | 1978-02-13 |
| SE376413B (enExample) | 1975-05-26 |
| AU4317672A (en) | 1973-12-13 |
| CH586652A5 (enExample) | 1977-04-15 |
| NL7208008A (enExample) | 1972-12-13 |
| CH587219A5 (enExample) | 1977-04-29 |
| DE2227842B2 (de) | 1975-03-27 |
| AT324317B (de) | 1975-08-25 |
| NO133972C (enExample) | 1976-07-28 |
| JPS525498B1 (enExample) | 1977-02-14 |
| NO133972B (enExample) | 1976-04-20 |
| CH577457A5 (enExample) | 1976-07-15 |
| AU471250B2 (en) | 1973-12-13 |
| FR2140662A1 (enExample) | 1973-01-19 |
| BE784719A (fr) | 1972-12-12 |
| BE784718A (fr) | 1972-12-12 |
| DE2227842A1 (de) | 1972-12-21 |
| CH587218A5 (enExample) | 1977-04-29 |
| GB1372644A (en) | 1974-11-06 |
| DK136243B (da) | 1977-09-12 |
| CA1005075A (en) | 1977-02-08 |
| FR2140662B1 (enExample) | 1976-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |