DE2029297A1 - Neue Aminophenyl-cycloamidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel - Google Patents
Neue Aminophenyl-cycloamidine, Verfahren zu ihrer Herstellung und ihre Verwendung als ArzneimittelInfo
- Publication number
- DE2029297A1 DE2029297A1 DE19702029297 DE2029297A DE2029297A1 DE 2029297 A1 DE2029297 A1 DE 2029297A1 DE 19702029297 DE19702029297 DE 19702029297 DE 2029297 A DE2029297 A DE 2029297A DE 2029297 A1 DE2029297 A1 DE 2029297A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- groups
- methyl
- general formula
- 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
- 238000000034 method Methods 0.000 title claims description 20
- 239000003814 drug Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000003951 lactams Chemical class 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims 4
- 229940127089 cytotoxic agent Drugs 0.000 claims 4
- AOBVUTGWKRRSRO-UHFFFAOYSA-N 2-[6-[[4-[(2-bromoacetyl)amino]phenyl]methyl]-4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CCN(CC(O)=O)C1CC1=CC=C(NC(=O)CBr)C=C1 AOBVUTGWKRRSRO-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 15
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 241001465677 Ancylostomatoidea Species 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241001494479 Pecora Species 0.000 description 6
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- SABZQUOBNXDLDV-UHFFFAOYSA-N ethyl n-(4-aminophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(N)C=C1 SABZQUOBNXDLDV-UHFFFAOYSA-N 0.000 description 5
- 244000045947 parasite Species 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- HVCNPAUSWKHWAA-UHFFFAOYSA-N 4-[(1-methylpyrrolidin-2-ylidene)amino]aniline Chemical compound CN1CCCC1=NC1=CC=C(N)C=C1 HVCNPAUSWKHWAA-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- RMCDISSZWOPOIH-UHFFFAOYSA-N ethyl N-[4-[(1-methylpyrrolidin-2-ylidene)amino]phenyl]carbamate Chemical compound C(=O)(OCC)NC1=CC=C(C=C1)N=C1N(CCC1)C RMCDISSZWOPOIH-UHFFFAOYSA-N 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 244000000013 helminth Species 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- 150000003840 hydrochlorides Chemical class 0.000 description 3
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- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
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- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 2
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
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- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000191771 Teladorsagia circumcincta Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000607143 Toxascaris leonina Species 0.000 description 1
- 241000244030 Toxocara canis Species 0.000 description 1
- 241000243792 Trichostrongylidae Species 0.000 description 1
- 241000571980 Uncinaria stenocephala Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- NFOQJNGQQXICBY-UHFFFAOYSA-N dimethyl 2-methylbutanedioate Chemical compound COC(=O)CC(C)C(=O)OC NFOQJNGQQXICBY-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WFOSPQMHDQYLIC-UHFFFAOYSA-N ethyl N-[4-(3,4-dihydro-2H-pyrrol-5-ylamino)phenyl]carbamate Chemical compound C(=O)(OCC)NC1=CC=C(C=C1)N=C1NCCC1 WFOSPQMHDQYLIC-UHFFFAOYSA-N 0.000 description 1
- XNKCQZQMQUOCML-UHFFFAOYSA-N ethyl n-(4-amino-2,6-dimethylphenyl)carbamate Chemical compound CCOC(=O)NC1=C(C)C=C(N)C=C1C XNKCQZQMQUOCML-UHFFFAOYSA-N 0.000 description 1
- WOJPKCLHZYLNGK-UHFFFAOYSA-N ethyl n-(4-isocyanatophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(N=C=O)C=C1 WOJPKCLHZYLNGK-UHFFFAOYSA-N 0.000 description 1
- 229940093470 ethylene Drugs 0.000 description 1
- 238000002474 experimental method Methods 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
- 210000003608 fece Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- LABMCLJKOMAZCZ-UHFFFAOYSA-N n'-phenylbutanehydrazide Chemical compound CCCC(=O)NNC1=CC=CC=C1 LABMCLJKOMAZCZ-UHFFFAOYSA-N 0.000 description 1
- LWSZSITZAHAJAQ-UHFFFAOYSA-N n'-phenylethanesulfonohydrazide Chemical compound CCS(=O)(=O)NNC1=CC=CC=C1 LWSZSITZAHAJAQ-UHFFFAOYSA-N 0.000 description 1
- UQPFSVMPYHXOFG-UHFFFAOYSA-N n'-phenylmethanesulfonohydrazide Chemical compound CS(=O)(=O)NNC1=CC=CC=C1 UQPFSVMPYHXOFG-UHFFFAOYSA-N 0.000 description 1
- AQNIKHBQYCPLDZ-UHFFFAOYSA-N n'-phenylprop-2-enehydrazide Chemical compound C=CC(=O)NNC1=CC=CC=C1 AQNIKHBQYCPLDZ-UHFFFAOYSA-N 0.000 description 1
- HXAKXFPOKDRNCQ-UHFFFAOYSA-N n'-phenylpropanehydrazide Chemical compound CCC(=O)NNC1=CC=CC=C1 HXAKXFPOKDRNCQ-UHFFFAOYSA-N 0.000 description 1
- QFELUFGHFLYZEZ-UHFFFAOYSA-N n-(4-aminophenyl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=C(N)C=C1 QFELUFGHFLYZEZ-UHFFFAOYSA-N 0.000 description 1
- ZTRARGHXCLHSIQ-UHFFFAOYSA-N n-phenyl-3,4-dihydro-2h-pyrrol-5-amine Chemical class C1CCN=C1NC1=CC=CC=C1 ZTRARGHXCLHSIQ-UHFFFAOYSA-N 0.000 description 1
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical group CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000005824 oxyalkoxy group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Saccharide Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702029297 DE2029297A1 (de) | 1970-06-13 | 1970-06-13 | Neue Aminophenyl-cycloamidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AR236167A AR206281A1 (es) | 1970-06-13 | 1971-01-01 | Procedimiento para la produccion de nuevas amino-fenil-imino-pirrolidinas |
| US00151576A US3769274A (en) | 1970-06-13 | 1971-06-09 | Aminophenyl-cycloamidines |
| SU1670622A SU404240A1 (ru) | 1971-06-09 | Способ получения аминофепил-циклоамидинов или их солей | |
| SU1839951A SU439975A3 (ru) | 1970-06-13 | 1971-06-09 | Способ получения аминофенилциклоамидинов или их солей |
| EG249/71A EG10780A (en) | 1970-06-13 | 1971-06-10 | Process for preparation of aminophenyl amidines used as parasiticides and hypotensive agents |
| ZA713764A ZA713764B (en) | 1970-06-13 | 1971-06-10 | New aminophenyl-cycloamidines,their production and their medicinal use |
| GB2749471A GB1325528A (en) | 1970-06-13 | 1971-06-11 | Aminophenylcycloamidine derivatives their production and their medicinal use |
| CS5023A CS172347B2 (en, 2012) | 1970-06-13 | 1971-06-11 | |
| AT503971A AT303024B (de) | 1970-06-13 | 1971-06-11 | Verfahren zur Herstellung von neuen Aminophenyl-cycloamidinen und ihren Salzen |
| IE756/71A IE35361B1 (en) | 1970-06-13 | 1971-06-11 | New aminophenyl-cycloamidine derivatives, their production and their medicinal use |
| FR7121383A FR2100755B1 (en, 2012) | 1970-06-13 | 1971-06-11 | |
| CA115,439A CA942312A (en) | 1970-06-13 | 1971-06-11 | Aminophenyl-cycloamidines, their production and their medicinal use |
| CH856571A CH560683A5 (en, 2012) | 1970-06-13 | 1971-06-11 | |
| SE7107598A SE370939B (en, 2012) | 1970-06-13 | 1971-06-11 | |
| CS4322A CS172346B2 (en, 2012) | 1970-06-13 | 1971-06-11 | |
| BE768401A BE768401A (fr) | 1970-06-13 | 1971-06-11 | Nouvelles aminophenyl-cycloamidines vermifuges et leur obtention |
| AT244672A AT310729B (de) | 1970-06-13 | 1971-06-11 | Verfahren zur Herstellung von neuen Aminophenyl-cycloamidinen und ihren Salzen |
| CH811074A CH566982A5 (en, 2012) | 1970-06-13 | 1971-06-11 | |
| NL7108067A NL7108067A (en, 2012) | 1970-06-13 | 1971-06-11 | |
| PL1971148771A PL76889B1 (en, 2012) | 1970-06-13 | 1971-06-12 | |
| RO67285A RO61934A (en, 2012) | 1970-06-13 | 1971-06-12 | |
| RO71327A RO58736A (en, 2012) | 1970-06-13 | 1971-06-12 | |
| ES392165A ES392165A1 (es) | 1970-06-13 | 1971-06-12 | Procedimiento para la produccion de aminofenil-cincloamidi-nas. |
| PH12539A PH10935A (en) | 1970-06-13 | 1971-06-14 | Aminophenyl-cycloamidines,anthelmintic compositions and method of using the same |
| JP4173571A JPS5416496B1 (en, 2012) | 1970-06-13 | 1971-06-14 | |
| ES402567A ES402567A1 (es) | 1970-06-13 | 1972-05-09 | Procedimiento para la produccion de aminofenil-cicloamidi- nas. |
| AR243280A AR202376A1 (es) | 1970-06-13 | 1972-07-26 | Procedimiento para la produccion de nuevas aminofenil-imino-pirrolidinas |
| JP10193878A JPS5444663A (en) | 1970-06-13 | 1978-08-23 | Manufacture of aminophenyllcycloamidine and its salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702029297 DE2029297A1 (de) | 1970-06-13 | 1970-06-13 | Neue Aminophenyl-cycloamidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2029297A1 true DE2029297A1 (de) | 1971-12-30 |
Family
ID=5773919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702029297 Pending DE2029297A1 (de) | 1970-06-13 | 1970-06-13 | Neue Aminophenyl-cycloamidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3769274A (en, 2012) |
| JP (2) | JPS5416496B1 (en, 2012) |
| AR (2) | AR206281A1 (en, 2012) |
| AT (2) | AT303024B (en, 2012) |
| BE (1) | BE768401A (en, 2012) |
| CA (1) | CA942312A (en, 2012) |
| CH (2) | CH560683A5 (en, 2012) |
| CS (2) | CS172346B2 (en, 2012) |
| DE (1) | DE2029297A1 (en, 2012) |
| EG (1) | EG10780A (en, 2012) |
| ES (2) | ES392165A1 (en, 2012) |
| FR (1) | FR2100755B1 (en, 2012) |
| GB (1) | GB1325528A (en, 2012) |
| IE (1) | IE35361B1 (en, 2012) |
| NL (1) | NL7108067A (en, 2012) |
| PH (1) | PH10935A (en, 2012) |
| PL (1) | PL76889B1 (en, 2012) |
| RO (2) | RO58736A (en, 2012) |
| SE (1) | SE370939B (en, 2012) |
| SU (1) | SU439975A3 (en, 2012) |
| ZA (1) | ZA713764B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2801051A1 (fr) * | 1999-11-17 | 2001-05-18 | Adir | Nouveaux composes aminopyrroline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2002020526A3 (en) * | 2000-09-07 | 2002-05-30 | Bayer Ag | Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binding agents |
| DE102008030764A1 (de) | 2008-06-28 | 2009-12-31 | Bayer Animal Health Gmbh | Kombination von Amidin-Derivaten mit cyclischen Depsipeptiden |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013676A (en) * | 1970-06-13 | 1977-03-22 | Bayer Aktiengesellschaft | Aminophenylamidines, their production and their pharmaceutical use |
| US3911010A (en) * | 1970-06-13 | 1975-10-07 | Bayer Ag | Aminophenylamidines, their production and their pharmaceutical use |
| US4018814A (en) * | 1970-06-13 | 1977-04-19 | Bayer Aktiengesellschaft | Aromatic amides and carbomates of phenylamidines |
| US4533739A (en) * | 1982-10-12 | 1985-08-06 | G. D. Searle & Co. | 2-[(Aminophenyl and amidophenyl)amino]-1-azacycloalkanes having antidiarrheal activity |
| US4579951A (en) * | 1984-03-19 | 1986-04-01 | G. D. Searle & Co. | Substituted (azacycloalk-2-yl)iminophenols and esters thereof |
| JPS61106073U (en, 2012) * | 1984-12-19 | 1986-07-05 | ||
| GB8903592D0 (en) * | 1989-02-16 | 1989-04-05 | Boots Co Plc | Therapeutic agents |
| US5344933A (en) * | 1991-09-11 | 1994-09-06 | Fuji Photo Film Co., Ltd. | Pyrrole ring-or condensed pyrrole ring-containing azomethine dye |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670859A1 (de) * | 1967-04-24 | 1971-03-11 | Bayer Ag | Verfahren zur Herstellung von 2-Phenyl-imino-1-azacycloalkanen |
-
1970
- 1970-06-13 DE DE19702029297 patent/DE2029297A1/de active Pending
-
1971
- 1971-01-01 AR AR236167A patent/AR206281A1/es active
- 1971-06-09 US US00151576A patent/US3769274A/en not_active Expired - Lifetime
- 1971-06-09 SU SU1839951A patent/SU439975A3/ru active
- 1971-06-10 EG EG249/71A patent/EG10780A/xx active
- 1971-06-10 ZA ZA713764A patent/ZA713764B/xx unknown
- 1971-06-11 GB GB2749471A patent/GB1325528A/en not_active Expired
- 1971-06-11 FR FR7121383A patent/FR2100755B1/fr not_active Expired
- 1971-06-11 AT AT503971A patent/AT303024B/de not_active IP Right Cessation
- 1971-06-11 CH CH856571A patent/CH560683A5/xx not_active IP Right Cessation
- 1971-06-11 NL NL7108067A patent/NL7108067A/xx not_active Application Discontinuation
- 1971-06-11 SE SE7107598A patent/SE370939B/xx unknown
- 1971-06-11 CS CS4322A patent/CS172346B2/cs unknown
- 1971-06-11 AT AT244672A patent/AT310729B/de not_active IP Right Cessation
- 1971-06-11 CH CH811074A patent/CH566982A5/xx not_active IP Right Cessation
- 1971-06-11 IE IE756/71A patent/IE35361B1/xx unknown
- 1971-06-11 BE BE768401A patent/BE768401A/xx unknown
- 1971-06-11 CS CS5023A patent/CS172347B2/cs unknown
- 1971-06-11 CA CA115,439A patent/CA942312A/en not_active Expired
- 1971-06-12 ES ES392165A patent/ES392165A1/es not_active Expired
- 1971-06-12 RO RO71327A patent/RO58736A/ro unknown
- 1971-06-12 RO RO67285A patent/RO61934A/ro unknown
- 1971-06-12 PL PL1971148771A patent/PL76889B1/pl unknown
- 1971-06-14 JP JP4173571A patent/JPS5416496B1/ja active Pending
- 1971-06-14 PH PH12539A patent/PH10935A/en unknown
-
1972
- 1972-05-09 ES ES402567A patent/ES402567A1/es not_active Expired
- 1972-07-26 AR AR243280A patent/AR202376A1/es active
-
1978
- 1978-08-23 JP JP10193878A patent/JPS5444663A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2801051A1 (fr) * | 1999-11-17 | 2001-05-18 | Adir | Nouveaux composes aminopyrroline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1101756A1 (fr) * | 1999-11-17 | 2001-05-23 | Adir Et Compagnie | Nouveaux composés aminopyrroline, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| WO2002020526A3 (en) * | 2000-09-07 | 2002-05-30 | Bayer Ag | Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binding agents |
| DE102008030764A1 (de) | 2008-06-28 | 2009-12-31 | Bayer Animal Health Gmbh | Kombination von Amidin-Derivaten mit cyclischen Depsipeptiden |
Also Published As
| Publication number | Publication date |
|---|---|
| AT310729B (de) | 1973-10-10 |
| CS172347B2 (en, 2012) | 1976-12-29 |
| JPS5420492B2 (en, 2012) | 1979-07-23 |
| IE35361L (en) | 1971-12-13 |
| AT303024B (de) | 1972-11-10 |
| FR2100755B1 (en, 2012) | 1974-10-18 |
| ES402567A1 (es) | 1975-03-16 |
| JPS5444663A (en) | 1979-04-09 |
| CH566982A5 (en, 2012) | 1975-09-30 |
| AR206281A1 (es) | 1976-07-15 |
| RO58736A (en, 2012) | 1976-01-15 |
| ES392165A1 (es) | 1974-02-01 |
| RO61934A (en, 2012) | 1977-08-15 |
| AR202376A1 (es) | 1975-06-06 |
| SU404240A3 (en, 2012) | 1973-10-26 |
| EG10780A (en) | 1976-08-31 |
| FR2100755A1 (en, 2012) | 1972-03-24 |
| SE370939B (en, 2012) | 1974-11-04 |
| BE768401A (fr) | 1971-12-13 |
| CH560683A5 (en, 2012) | 1975-04-15 |
| GB1325528A (en) | 1973-08-01 |
| IE35361B1 (en) | 1976-01-21 |
| SU439975A3 (ru) | 1974-08-15 |
| PL76889B1 (en, 2012) | 1975-02-28 |
| JPS5416496B1 (en, 2012) | 1979-06-22 |
| NL7108067A (en, 2012) | 1971-12-15 |
| PH10935A (en) | 1977-10-05 |
| ZA713764B (en) | 1972-01-26 |
| US3769274A (en) | 1973-10-30 |
| CS172346B2 (en, 2012) | 1976-12-29 |
| CA942312A (en) | 1974-02-19 |
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Legal Events
| Date | Code | Title | Description |
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