NO134421B - - Google Patents
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- Publication number
- NO134421B NO134421B NO574/70A NO57470A NO134421B NO 134421 B NO134421 B NO 134421B NO 574/70 A NO574/70 A NO 574/70A NO 57470 A NO57470 A NO 57470A NO 134421 B NO134421 B NO 134421B
- Authority
- NO
- Norway
- Prior art keywords
- dichlorophenyl
- compounds
- formula
- reacted
- methyl ester
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 22
- FCWRUYPZZJPCCG-UHFFFAOYSA-N methyl 2-(2,6-dichlorophenyl)acetate Chemical compound COC(=O)CC1=C(Cl)C=CC=C1Cl FCWRUYPZZJPCCG-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N methylguanidine Chemical compound CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N 1,1-dimethylguanidine Chemical compound CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 3
- -1 2-[2-(2,6-dichlorophenoxy)acetyl]-l-isopropylguanidine Chemical compound 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- ORAVVJNVOXLQIT-UHFFFAOYSA-N n-(diaminomethylidene)-2-phenylacetamide Chemical class NC(=N)NC(=O)CC1=CC=CC=C1 ORAVVJNVOXLQIT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- JDXXTKLHHZMVIO-UHFFFAOYSA-N 2-(3-hydroxypropyl)guanidine Chemical compound NC(=N)NCCCO JDXXTKLHHZMVIO-UHFFFAOYSA-N 0.000 claims 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 claims 1
- UZEKTDVGUQCDBI-UHFFFAOYSA-N 2-propan-2-ylguanidine Chemical compound CC(C)NC(N)=N UZEKTDVGUQCDBI-UHFFFAOYSA-N 0.000 claims 1
- BWMDMTSNSXYYSP-UHFFFAOYSA-N 2-propylguanidine Chemical compound CCCNC(N)=N BWMDMTSNSXYYSP-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 claims 1
- OGTSEJZIUMTBRW-UHFFFAOYSA-N n-[amino(dimethylamino)methylidene]-2-(2,6-dichlorophenyl)acetamide Chemical compound CN(C)C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl OGTSEJZIUMTBRW-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 136
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 230000036772 blood pressure Effects 0.000 description 7
- 229960000789 guanidine hydrochloride Drugs 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YMPKGRGRMBFGHC-UHFFFAOYSA-N methyl n'-[2-(2,6-dichlorophenyl)acetyl]carbamimidothioate Chemical compound CSC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl YMPKGRGRMBFGHC-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VFRDBQGBQYINBH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=C(Cl)C=CC=C1Cl VFRDBQGBQYINBH-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- KRYWEAYKLGCRRH-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]azanium;chloride Chemical compound Cl.CSC(N)=N KRYWEAYKLGCRRH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229960004198 guanidine Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000004317 sodium nitrate Substances 0.000 description 4
- 235000010344 sodium nitrate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 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 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- HIWRFMBBUWDNNB-UHFFFAOYSA-N Cl.CN(C(=N)NC)C Chemical compound Cl.CN(C(=N)NC)C HIWRFMBBUWDNNB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- INJOMKTZOLKMBF-UHFFFAOYSA-N Guanfacine Chemical compound NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl INJOMKTZOLKMBF-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- NIVZHWNOUVJHKV-UHFFFAOYSA-N bethanidine Chemical compound CN\C(=N/C)NCC1=CC=CC=C1 NIVZHWNOUVJHKV-UHFFFAOYSA-N 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- MCMBEBOHGREEOP-UHFFFAOYSA-N 1,2-diethylguanidine Chemical compound CCNC(=N)NCC MCMBEBOHGREEOP-UHFFFAOYSA-N 0.000 description 1
- BJYQZVHBGPJPID-UHFFFAOYSA-N 1,2-dimethylguanidine hydroiodide Chemical compound I.CNC(=N)NC BJYQZVHBGPJPID-UHFFFAOYSA-N 0.000 description 1
- WTYJBGQERCCGAD-UHFFFAOYSA-N 1-Methylguanidine sulfate (2:1) Chemical compound CN=C(N)N.CN=C(N)N.OS(O)(=O)=O WTYJBGQERCCGAD-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- OZZMCFALUZPONR-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-pyrimidin-2-ylacetamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)NC1=NC=CC=N1 OZZMCFALUZPONR-UHFFFAOYSA-N 0.000 description 1
- JXXQSFUWEIFWJY-UHFFFAOYSA-N 2-(2-hydroxyethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCO JXXQSFUWEIFWJY-UHFFFAOYSA-N 0.000 description 1
- DABOOPWKHPBSBV-UHFFFAOYSA-N 2-(2-hydroxypropyl)guanidine Chemical compound CC(O)CN=C(N)N DABOOPWKHPBSBV-UHFFFAOYSA-N 0.000 description 1
- HNLCDSMHFQUQNN-UHFFFAOYSA-N 2-(2-methoxyethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.COCCN=C(N)N HNLCDSMHFQUQNN-UHFFFAOYSA-N 0.000 description 1
- WPIAFQJDDMHIRG-UHFFFAOYSA-N 2-(2-methylpropyl)guanidine hydrochloride Chemical compound Cl.CC(C)CNC(N)=N WPIAFQJDDMHIRG-UHFFFAOYSA-N 0.000 description 1
- NKJPCFSNQMPRQN-UHFFFAOYSA-N 2-(3-hydroxypropyl)guanidine;nitric acid Chemical compound O[N+]([O-])=O.NC(N)=NCCCO NKJPCFSNQMPRQN-UHFFFAOYSA-N 0.000 description 1
- QWNCXLJBDCKTEI-UHFFFAOYSA-N 2-(3-methoxypropyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.COCCCN=C(N)N QWNCXLJBDCKTEI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- ABSNGNUGFQIDDO-UHFFFAOYSA-N 2-benzylguanidine Chemical class NC(N)=NCC1=CC=CC=C1 ABSNGNUGFQIDDO-UHFFFAOYSA-N 0.000 description 1
- PBWYKHZQEJXPAA-UHFFFAOYSA-N 2-butylguanidine;hydrochloride Chemical compound Cl.CCCCN=C(N)N PBWYKHZQEJXPAA-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ACAVKGZABJJJFG-UHFFFAOYSA-N 2-ethylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCN=C(N)N ACAVKGZABJJJFG-UHFFFAOYSA-N 0.000 description 1
- BVLXQZKQUIRWEI-UHFFFAOYSA-N 2-hexylguanidine Chemical compound CCCCCCN=C(N)N BVLXQZKQUIRWEI-UHFFFAOYSA-N 0.000 description 1
- SPEGGZARBJGNCD-UHFFFAOYSA-N 4,5-dihydro-1H-imidazol-2-amine sulfuric acid Chemical compound S(=O)(=O)(O)O.NC=1NCCN1 SPEGGZARBJGNCD-UHFFFAOYSA-N 0.000 description 1
- NRKTUPLYOCIVPP-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine;hydroiodide Chemical compound I.NC1=NCCN1 NRKTUPLYOCIVPP-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004980 betanidine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ACPFLXJEPKOPGF-UHFFFAOYSA-N diaminomethylidene(dimethyl)azanium;hydrogen sulfate Chemical compound [O-]S([O-])(=O)=O.C[NH+](C)C([NH3+])=N ACPFLXJEPKOPGF-UHFFFAOYSA-N 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940102253 isopropanolamine Drugs 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- FIURMSDYKUNVJC-UHFFFAOYSA-N methyl 2-(2,6-dimethylphenyl)acetate Chemical compound COC(=O)CC1=C(C)C=CC=C1C FIURMSDYKUNVJC-UHFFFAOYSA-N 0.000 description 1
- KHBWTRFWQROKJZ-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1Cl KHBWTRFWQROKJZ-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- NGGXACLSAZXJGM-UHFFFAOYSA-N n-(diaminomethylidene)acetamide Chemical class CC(=O)N=C(N)N NGGXACLSAZXJGM-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- OGRFBOIMUGHLSD-UHFFFAOYSA-N nitric acid 2-propan-2-ylguanidine Chemical compound [N+](=O)(O)[O-].C(C)(C)NC(=N)N OGRFBOIMUGHLSD-UHFFFAOYSA-N 0.000 description 1
- QWXFVBMIBKIJGA-UHFFFAOYSA-N nitric acid 2-propylguanidine Chemical compound [N+](=O)(O)[O-].C(CC)NC(=N)N QWXFVBMIBKIJGA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D247/00—Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00
- C07D247/02—Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00 having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/16—Nitrogen atoms not forming part of a nitro radical acylated on said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257569A CH511815A (de) | 1969-02-20 | 1969-02-20 | Verfahren zur Herstellung von Acylguanidinen |
| CH469169 | 1969-03-27 | ||
| CH1657569 | 1969-11-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134421B true NO134421B (de) | 1976-06-28 |
| NO134421C NO134421C (de) | 1976-10-06 |
Family
ID=27173786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO574/70A NO134421C (de) | 1969-02-20 | 1970-02-18 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3634508A (de) |
| AT (2) | AT309460B (de) |
| BE (1) | BE746168A (de) |
| CA (1) | CA952111A (de) |
| CS (2) | CS158263B2 (de) |
| DE (1) | DE2006895A1 (de) |
| DK (1) | DK129577B (de) |
| ES (4) | ES376661A1 (de) |
| FI (1) | FI48728C (de) |
| FR (1) | FR2034557B1 (de) |
| GB (1) | GB1298112A (de) |
| IL (1) | IL33925A (de) |
| NL (1) | NL7001836A (de) |
| NO (1) | NO134421C (de) |
| PL (1) | PL80868B1 (de) |
| SE (1) | SE352077B (de) |
| SU (2) | SU508182A3 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2408289A1 (de) * | 1974-02-21 | 1975-09-11 | Hoechst Ag | Substituierte diaminoguanidine und ihre herstellung |
| DE2901362A1 (de) * | 1978-01-25 | 1979-07-26 | Sandoz Ag | Guanidinderivate, ihre herstellung und verwendung |
| DE2931735A1 (de) * | 1979-08-04 | 1981-02-19 | Beiersdorf Ag | Neue substituierte phenylacetylguanidine und verfahren zu ihrer herstellung |
| US4332822A (en) * | 1980-02-05 | 1982-06-01 | John Wyeth & Brother Limited | Guanidine derivatives |
| DE3360148D1 (en) * | 1982-02-10 | 1985-06-05 | Beecham Group Plc | Guanidine derivatives |
| DE4421536A1 (de) * | 1994-06-20 | 1995-12-21 | Hoechst Ag | Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| GB0916163D0 (en) * | 2009-09-15 | 2009-10-28 | Shire Llc | Prodrugs of guanfacine |
| RS53373B (en) | 2009-12-16 | 2014-10-31 | Vivabiocell Spa | CONTINUOUS CULTIVATION DEVICE |
| CN102887838A (zh) * | 2012-10-29 | 2013-01-23 | 河南中帅医药科技发展有限公司 | 盐酸胍法辛的制备方法 |
| CN103058890A (zh) * | 2012-12-27 | 2013-04-24 | 郑州大明药物科技有限公司 | 盐酸胍法辛的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2408694A (en) * | 1942-05-29 | 1946-10-01 | Libbey Owens Ford Glass Co | Method of preparing acyl guanidines |
-
1970
- 1970-02-04 GB GB5422/70A patent/GB1298112A/en not_active Expired
- 1970-02-09 US US9973A patent/US3634508A/en not_active Expired - Lifetime
- 1970-02-10 NL NL7001836A patent/NL7001836A/xx unknown
- 1970-02-14 DE DE19702006895 patent/DE2006895A1/de active Pending
- 1970-02-18 FR FR7005762A patent/FR2034557B1/fr not_active Expired
- 1970-02-18 CA CA075,161A patent/CA952111A/en not_active Expired
- 1970-02-18 AT AT146970A patent/AT309460B/de not_active IP Right Cessation
- 1970-02-18 BE BE746168D patent/BE746168A/xx unknown
- 1970-02-18 SU SU1620864A patent/SU508182A3/ru active
- 1970-02-18 ES ES376661A patent/ES376661A1/es not_active Expired
- 1970-02-18 FI FI700435A patent/FI48728C/fi active
- 1970-02-18 PL PL1970138859A patent/PL80868B1/pl unknown
- 1970-02-18 IL IL33925A patent/IL33925A/en unknown
- 1970-02-18 CS CS112570A patent/CS158263B2/cs unknown
- 1970-02-18 NO NO574/70A patent/NO134421C/no unknown
- 1970-02-18 CS CS569072*1A patent/CS158264B2/cs unknown
- 1970-02-18 SU SU1406184A patent/SU453830A3/ru active
- 1970-02-18 AT AT983771A patent/AT309461B/de not_active IP Right Cessation
- 1970-02-19 SE SE02123/70A patent/SE352077B/xx unknown
- 1970-02-19 DK DK82670AA patent/DK129577B/da unknown
- 1970-10-14 ES ES384493A patent/ES384493A1/es not_active Expired
- 1970-10-14 ES ES384491A patent/ES384491A1/es not_active Expired
- 1970-10-14 ES ES384492A patent/ES384492A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI48728B (de) | 1974-09-02 |
| CS158264B2 (de) | 1974-10-15 |
| AT309460B (de) | 1973-08-27 |
| PL80868B1 (de) | 1975-08-30 |
| CS158263B2 (de) | 1974-10-15 |
| FI48728C (fi) | 1974-12-10 |
| ES384493A1 (es) | 1974-06-16 |
| DK129577B (da) | 1974-10-28 |
| US3634508A (en) | 1972-01-11 |
| DE2006895A1 (de) | 1970-09-10 |
| SU508182A3 (ru) | 1976-03-25 |
| ES384492A1 (es) | 1973-06-01 |
| SU453830A3 (ru) | 1974-12-15 |
| IL33925A (en) | 1973-08-29 |
| NL7001836A (de) | 1970-08-24 |
| NO134421C (de) | 1976-10-06 |
| FR2034557B1 (de) | 1973-12-21 |
| FR2034557A1 (de) | 1970-12-11 |
| AT309461B (de) | 1973-08-27 |
| SE352077B (de) | 1972-12-18 |
| CA952111A (en) | 1974-07-30 |
| ES384491A1 (es) | 1974-02-16 |
| IL33925A0 (en) | 1970-04-20 |
| BE746168A (fr) | 1970-08-18 |
| DK129577C (de) | 1975-03-24 |
| GB1298112A (en) | 1972-11-29 |
| ES376661A1 (es) | 1972-09-16 |
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