DE2519193A1 - Pharmazeutische produkte - Google Patents
Pharmazeutische produkteInfo
- Publication number
- DE2519193A1 DE2519193A1 DE19752519193 DE2519193A DE2519193A1 DE 2519193 A1 DE2519193 A1 DE 2519193A1 DE 19752519193 DE19752519193 DE 19752519193 DE 2519193 A DE2519193 A DE 2519193A DE 2519193 A1 DE2519193 A1 DE 2519193A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- substituted
- atom
- meaning
- 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.)
- Pending
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- 229940127557 pharmaceutical product Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 18
- -1 hydroxymethylene group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- 241000700159 Rattus Species 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000003814 drug Substances 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 210000003608 fece Anatomy 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000010871 livestock manure Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 208000006750 hematuria Diseases 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 210000003932 urinary bladder Anatomy 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 150000003939 benzylamines Chemical class 0.000 description 3
- 230000002308 calcification Effects 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229960002591 hydroxyproline Drugs 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PIINXYKJQGMIOZ-UHFFFAOYSA-N 1,2-dipyridin-2-ylethane-1,2-dione Chemical compound C=1C=CC=NC=1C(=O)C(=O)C1=CC=CC=N1 PIINXYKJQGMIOZ-UHFFFAOYSA-N 0.000 description 2
- OEPFPKVWOOSTBV-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)ethanamine Chemical compound COC1=CC=C(C(C)N)C=C1OC OEPFPKVWOOSTBV-UHFFFAOYSA-N 0.000 description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- 206010033892 Paraplegia Diseases 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000036528 appetite Effects 0.000 description 2
- 235000019789 appetite Nutrition 0.000 description 2
- 238000011888 autopsy Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- 229960005091 chloramphenicol Drugs 0.000 description 2
- 230000036570 collagen biosynthesis Effects 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229960000890 hydrocortisone Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 235000019364 tetracycline Nutrition 0.000 description 2
- 150000003522 tetracyclines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010008096 Cerebral atrophy Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 208000001778 Coronary Occlusion Diseases 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 230000003510 anti-fibrotic effect Effects 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 230000022159 cartilage development Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 231100000895 deafness Toxicity 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 208000016354 hearing loss disease Diseases 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 206010021654 increased appetite Diseases 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 210000001847 jaw Anatomy 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000002050 maxilla Anatomy 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- 210000000713 mesentery Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- BMNDJWSIKZECMH-UHFFFAOYSA-N nitrosyl bromide Chemical compound BrN=O BMNDJWSIKZECMH-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 229940126589 solid medicine Drugs 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07D295/125—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (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 |
---|---|---|---|
GB1915774A GB1529564A (en) | 1974-05-01 | 1974-05-01 | Pharmaceutical compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2519193A1 true DE2519193A1 (de) | 1975-11-20 |
Family
ID=10124714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752519193 Pending DE2519193A1 (de) | 1974-05-01 | 1975-04-30 | Pharmazeutische produkte |
Country Status (11)
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3104883A1 (de) * | 1980-02-12 | 1982-01-07 | Synthelabo S.A., 75007 Paris | Benzylidenderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
EP0609032A1 (en) * | 1993-01-25 | 1994-08-03 | Norsk Hydro A/S | Aromatic imine compounds, pharmaceutical composition thereof, useful as protein synthesis inhibitors |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2418222A2 (fr) * | 1975-08-01 | 1979-09-21 | Synthelabo | Procede de preparation de derives benzylideniques |
JPS52159599U (enrdf_load_stackoverflow) * | 1976-05-27 | 1977-12-03 | ||
JPS5812993Y2 (ja) * | 1978-07-19 | 1983-03-12 | 日本鋼管株式会社 | 吊下開閉式足場装置 |
FR2544308B1 (fr) * | 1983-04-14 | 1985-06-14 | Synthelabo | Ethines substituees, leur preparation et leur application en therapeutique |
-
1974
- 1974-05-01 GB GB1915774A patent/GB1529564A/en not_active Expired
-
1975
- 1975-04-26 EG EG25475A patent/EG12028A/xx active
- 1975-04-29 BE BE155898A patent/BE828530A/xx unknown
- 1975-04-30 DE DE19752519193 patent/DE2519193A1/de active Pending
- 1975-04-30 FR FR7513529A patent/FR2282870A1/fr active Granted
- 1975-04-30 ES ES437363A patent/ES437363A1/es not_active Expired
- 1975-04-30 CA CA225,873A patent/CA1060438A/en not_active Expired
- 1975-05-01 AU AU80721/75A patent/AU502579B2/en not_active Expired
- 1975-05-01 NL NL7505174A patent/NL7505174A/xx not_active Application Discontinuation
- 1975-05-01 JP JP5308975A patent/JPS5112933A/ja active Pending
- 1975-05-01 NZ NZ17738475A patent/NZ177384A/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3104883A1 (de) * | 1980-02-12 | 1982-01-07 | Synthelabo S.A., 75007 Paris | Benzylidenderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
EP0609032A1 (en) * | 1993-01-25 | 1994-08-03 | Norsk Hydro A/S | Aromatic imine compounds, pharmaceutical composition thereof, useful as protein synthesis inhibitors |
Also Published As
Publication number | Publication date |
---|---|
GB1529564A (en) | 1978-10-25 |
AU502579B2 (en) | 1979-08-02 |
FR2282870B1 (enrdf_load_stackoverflow) | 1978-11-10 |
AU8072175A (en) | 1976-11-04 |
BE828530A (fr) | 1975-10-29 |
FR2282870A1 (fr) | 1976-03-26 |
EG12028A (en) | 1978-06-30 |
CA1060438A (en) | 1979-08-14 |
ES437363A1 (es) | 1977-05-16 |
NZ177384A (en) | 1978-03-06 |
NL7505174A (nl) | 1975-11-04 |
JPS5112933A (ja) | 1976-01-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69433714T2 (de) | Kalzium - receptor aktive arylalkylamine | |
DE2357757A1 (de) | Substituierte acylanilide | |
DE2921072A1 (de) | Phenoxyalkylcarbonsaeure-derivate und diese verbindungen enthaltende arzneimittel | |
EP0002495B1 (de) | Erzeugnisse zur Anwendung in der cytostatischen Therapie | |
DE3424781C2 (de) | Verwendung von L-Carnosin zur Tumorbehandlung | |
DE2643936A1 (de) | Arzneimittel mit erythropoietischer wirksamkeit | |
DE2707831C2 (de) | 1-Nitro-9-Alkylaminoalkylaminoacridine, ihre Salze, Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung | |
DE2438399C3 (de) | a-substituierte Benzhydrolderivate und ihre Salze, solche enthaltende Arzneimittel und Verfahren zur Herstellung derselben | |
DE2519193A1 (de) | Pharmazeutische produkte | |
DE2921660A1 (de) | 5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel | |
DE2501834A1 (de) | Neue carbonsaeureverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel | |
DE69716914T2 (de) | Behandlung und prophylaxe von unerwünschten effekten reaktiver sauerstoffverbindungen | |
DE2034640C3 (de) | l-p-(7-Trifluormethyl-4-chinolyl) -amino-benzoyl-piperazine, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Bluthochdruck | |
AT391699B (de) | Verfahren zur herstellung neuer 4-chloro substituierter furo-(3,4-c)-pyridinderivate | |
DE2166359A1 (de) | Bis- eckige klammer auf (4-acylamidophenoxy)-alkyl eckige klammer zu -aether und ein verfahren zu ihrer herstellung | |
DE1493083B1 (de) | Linolsaeureamide und Verfahren zu ihrer Herstellung | |
DE2113489C3 (de) | 2-Nitro-benzofuranderivate, ein Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
DE1695284B2 (de) | Substituierte-2-amino-4,5-diphenyl- oxazolderivate | |
DE2221281C3 (de) | Pharmazeutische Zubereitungen mit entzündungshemmender und analgetischer Wirkung | |
DE1912130A1 (de) | Cholinoleat und Mittel zur Behandlung von Krankheiten der Leber,der Gallenblase und der Bauchspeicheldruese | |
DE2919553A1 (de) | Tetrahydroisochinolinderivat, verfahren zu seiner herstellung und es enthaltende arzneimittel | |
EP0121856A2 (de) | Verwendung von Pyrazolonderivaten bei der Bekämpfung des Wachstums von Tumorzellen und der Metastasenbildung, Arzneimittel hierfür und Verfahren zu deren Herstellung | |
AT329551B (de) | Verfahren zur herstellung neuer derivate des n-phenyl-n-alkanoyl-2-aminoindans | |
AT338781B (de) | Verfahren zur herstellung neuer 1,3-benzodioxol-derivate und ihrer salze | |
AT347456B (de) | Verfahren zur herstellung von neuen 5-methyl-7- hydroxy-isoflavon-derivaten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
OHJ | Non-payment of the annual fee |