DE1811832A1 - Neue Pyrrolidinoguandidine und Verfahren zu ihrer Herstellung - Google Patents
Neue Pyrrolidinoguandidine und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1811832A1 DE1811832A1 DE19681811832 DE1811832A DE1811832A1 DE 1811832 A1 DE1811832 A1 DE 1811832A1 DE 19681811832 DE19681811832 DE 19681811832 DE 1811832 A DE1811832 A DE 1811832A DE 1811832 A1 DE1811832 A1 DE 1811832A1
- Authority
- DE
- Germany
- Prior art keywords
- acid addition
- addition salts
- toxic acid
- guanidinoethyl
- carbon atoms
- 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title abstract description 56
- 208000001953 Hypotension Diseases 0.000 title abstract 2
- 208000021822 hypotensive Diseases 0.000 title abstract 2
- 230000001077 hypotensive effect Effects 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 38
- 231100000252 nontoxic Toxicity 0.000 claims description 24
- 230000003000 nontoxic effect Effects 0.000 claims description 24
- -1 pyrrolide alkylamine Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- KTDKAQFODMVOLP-UHFFFAOYSA-N 2-pyrrolidin-1-ylguanidine Chemical class NC(=N)NN1CCCC1 KTDKAQFODMVOLP-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001912 cyanamides Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical compound NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 claims description 3
- GAZRNXIMWKZADY-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide Chemical compound CC=1C=C(C)N(C(N)=N)N=1 GAZRNXIMWKZADY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 claims 1
- SMJYKQCVYOFCBF-UHFFFAOYSA-N CC1CN(CCCNC(N)=N)C(C)C1 Chemical compound CC1CN(CCCNC(N)=N)C(C)C1 SMJYKQCVYOFCBF-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 124
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 36
- 239000000203 mixture Substances 0.000 abstract description 34
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 15
- 239000003054 catalyst Substances 0.000 abstract description 9
- 229910052703 rhodium Inorganic materials 0.000 abstract description 6
- XZUAPPXGIFNDRA-UHFFFAOYSA-N ethane-1,2-diamine;hydrate Chemical compound O.NCCN XZUAPPXGIFNDRA-UHFFFAOYSA-N 0.000 abstract description 3
- PIBIHODWSMJTFG-UHFFFAOYSA-N 1-chloro-2-methylbut-3-yn-2-ol Chemical compound ClCC(O)(C)C#C PIBIHODWSMJTFG-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 53
- 238000009835 boiling Methods 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 35
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- 229910001868 water Inorganic materials 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 229910052717 sulfur Inorganic materials 0.000 description 26
- 238000000354 decomposition reaction Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 18
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 12
- 150000003233 pyrroles Chemical class 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 150000003235 pyrrolidines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 239000010948 rhodium Substances 0.000 description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
- XEBHIUPTXHNYOD-UHFFFAOYSA-N 1-chloro-2-methylpent-4-yn-2-ol Chemical compound ClCC(O)(C)CC#C XEBHIUPTXHNYOD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 4
- LOKVPVIVVXVDKQ-UHFFFAOYSA-N 2-(2,4-dimethylpyrrolidin-1-yl)ethanamine Chemical compound CC1CC(C)N(CCN)C1 LOKVPVIVVXVDKQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ISNDLTAVWAJSGJ-UHFFFAOYSA-N 2-(2,3-dimethylpyrrolidin-1-yl)ethanamine Chemical compound CC1CCN(CCN)C1C ISNDLTAVWAJSGJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ZWCHLOKPLFVXNK-UHFFFAOYSA-N 2-chloro-3-methylhex-5-yn-3-ol Chemical compound CC(Cl)C(C)(O)CC#C ZWCHLOKPLFVXNK-UHFFFAOYSA-N 0.000 description 2
- CXZJOMXTSWZMBZ-UHFFFAOYSA-N 2-tert-butyl-2-prop-2-ynyloxirane Chemical compound C#CCC1(C(C)(C)C)CO1 CXZJOMXTSWZMBZ-UHFFFAOYSA-N 0.000 description 2
- UOSRYHYUPWRJEK-UHFFFAOYSA-N 3-(chloromethyl)-2,2-dimethylhex-5-yn-3-ol Chemical compound CC(C)(C)C(O)(CCl)CC#C UOSRYHYUPWRJEK-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- FVDGTLHSSRKHBI-UHFFFAOYSA-N hydrogen sulfate;pyrrolidin-1-ium Chemical compound C1CC[NH2+]C1.OS([O-])(=O)=O FVDGTLHSSRKHBI-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- FNZNHTIBNDAHFH-UHFFFAOYSA-N n'-cyclohexyl-n'-methylethane-1,2-diamine Chemical compound NCCN(C)C1CCCCC1 FNZNHTIBNDAHFH-UHFFFAOYSA-N 0.000 description 2
- DJZWNSRUEJSEEB-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)nitramide Chemical compound [O-][N+](=O)NC1=NCCN1 DJZWNSRUEJSEEB-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- WMZWJUYJXQLURX-UHFFFAOYSA-N 1-chloro-2-methylhex-3-yn-2-ol Chemical compound CCC#CC(C)(O)CCl WMZWJUYJXQLURX-UHFFFAOYSA-N 0.000 description 1
- ULSAJQMHTGKPIY-UHFFFAOYSA-N 1-chloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CCl ULSAJQMHTGKPIY-UHFFFAOYSA-N 0.000 description 1
- WBTZYHJKPKGJDV-UHFFFAOYSA-N 1-chloropentan-3-ol Chemical compound CCC(O)CCCl WBTZYHJKPKGJDV-UHFFFAOYSA-N 0.000 description 1
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 1
- YBEGSYGMFWQLDQ-UHFFFAOYSA-N 2-(2,3-dimethylpyrrol-1-yl)ethanamine Chemical compound CC=1C=CN(CCN)C=1C YBEGSYGMFWQLDQ-UHFFFAOYSA-N 0.000 description 1
- GUIDIZDSHJFDFN-UHFFFAOYSA-N 2-(3-ethylpyrrol-1-yl)ethanamine Chemical compound CCC=1C=CN(CCN)C=1 GUIDIZDSHJFDFN-UHFFFAOYSA-N 0.000 description 1
- DXDQFNSYQQZGCG-UHFFFAOYSA-N 2-(3-methylpyrrolidin-1-yl)ethanamine Chemical compound CC1CCN(CCN)C1 DXDQFNSYQQZGCG-UHFFFAOYSA-N 0.000 description 1
- XOWQVCQUCJSEMY-UHFFFAOYSA-N 3,4-dimethylpyrazole-1-carboximidamide Chemical compound CC1=CN(C(N)=N)N=C1C XOWQVCQUCJSEMY-UHFFFAOYSA-N 0.000 description 1
- CMGFSOAWZMKIEI-UHFFFAOYSA-N 3-(2,4-dimethylpyrrol-1-yl)propan-1-amine Chemical compound Cc1cc(C)n(CCCN)c1 CMGFSOAWZMKIEI-UHFFFAOYSA-N 0.000 description 1
- DNFORMPUDIVIFO-UHFFFAOYSA-N 3-(2,4-dimethylpyrrolidin-1-yl)propan-1-amine Chemical compound CC1CC(C)N(CCCN)C1 DNFORMPUDIVIFO-UHFFFAOYSA-N 0.000 description 1
- XEALFIPMTNLHDK-UHFFFAOYSA-N 3-(chloromethyl)hept-1-yn-3-ol Chemical compound CCCCC(O)(CCl)C#C XEALFIPMTNLHDK-UHFFFAOYSA-N 0.000 description 1
- DDYITUDMFJPGJA-UHFFFAOYSA-N 3-(chloromethyl)hex-1-yn-3-ol Chemical compound ClCC(C#C)(CCC)O DDYITUDMFJPGJA-UHFFFAOYSA-N 0.000 description 1
- ZBPJPJNOUSGZJN-UHFFFAOYSA-N 3-(chloromethyl)hex-5-yn-3-ol Chemical compound CCC(O)(CCl)CC#C ZBPJPJNOUSGZJN-UHFFFAOYSA-N 0.000 description 1
- BUFJYUHTHJQPAT-UHFFFAOYSA-N 3-(chloromethyl)pent-1-yn-3-ol Chemical compound CCC(O)(CCl)C#C BUFJYUHTHJQPAT-UHFFFAOYSA-N 0.000 description 1
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 1
- ZILQRIKYRNQQDE-UHFFFAOYSA-N 4-(2-piperidin-4-ylethyl)piperidine Chemical compound C1CNCCC1CCC1CCNCC1 ZILQRIKYRNQQDE-UHFFFAOYSA-N 0.000 description 1
- CDJHACPKKUHUSX-UHFFFAOYSA-N 4-chloro-3-methylpent-1-yn-3-ol Chemical compound ClC(C(C#C)(O)C)C CDJHACPKKUHUSX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- YBRJAAAQWFQJRU-UHFFFAOYSA-N CC=1C=CN(CCN)C=1 Chemical compound CC=1C=CN(CCN)C=1 YBRJAAAQWFQJRU-UHFFFAOYSA-N 0.000 description 1
- NJYOENYANQQIAS-UHFFFAOYSA-N ClC(C#CCCC)(C)O Chemical compound ClC(C#CCCC)(C)O NJYOENYANQQIAS-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UNRBEYYLYRXYCG-ZETCQYMHSA-N [(2s)-1-ethylpyrrolidin-2-yl]methanamine Chemical compound CCN1CCC[C@H]1CN UNRBEYYLYRXYCG-ZETCQYMHSA-N 0.000 description 1
- NYMQJWVULPQXBK-UHFFFAOYSA-N [[amino(methylsulfanyl)methylidene]amino]azanium;iodide Chemical compound [I-].CSC(N)=[NH+]N NYMQJWVULPQXBK-UHFFFAOYSA-N 0.000 description 1
- NQXCSESBQRVSNS-UHFFFAOYSA-N ac1lhtnh Chemical compound C1N(C2)CN3CC1(C)CC2(C)C3 NQXCSESBQRVSNS-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- YLERVAXAQFOFRI-UHFFFAOYSA-M magnesium;propa-1,2-diene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C#C YLERVAXAQFOFRI-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YEMKVBRHRNHHGE-UHFFFAOYSA-N n-methyl-1-(1-methylpyrrol-2-yl)methanamine Chemical compound CNCC1=CC=CN1C YEMKVBRHRNHHGE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 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
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012609 strong anion exchange resin Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/06—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 no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB55708/67A GB1185080A (en) | 1967-12-07 | 1967-12-07 | Pyrrolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1811832A1 true DE1811832A1 (de) | 1969-07-03 |
Family
ID=10474656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681811832 Pending DE1811832A1 (de) | 1967-12-07 | 1968-11-29 | Neue Pyrrolidinoguandidine und Verfahren zu ihrer Herstellung |
Country Status (16)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0213326A1 (de) * | 1985-08-02 | 1987-03-11 | CASSELLA Aktiengesellschaft | 2,5-Dimethylpyrrolderivative, ihre Herstellung und ihre Verwendung |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW224974B (enrdf_load_stackoverflow) * | 1991-07-02 | 1994-06-11 | Hoffmann La Roche | |
| GB9803536D0 (en) * | 1998-02-19 | 1998-04-15 | Black James Foundation | Histamine H,receptor ligands |
-
1967
- 1967-12-07 GB GB55708/67A patent/GB1185080A/en not_active Expired
-
1968
- 1968-11-28 IE IE1454/68A patent/IE32781B1/xx unknown
- 1968-11-29 DE DE19681811832 patent/DE1811832A1/de active Pending
- 1968-12-02 IS IS1807A patent/IS1807A7/is unknown
- 1968-12-03 NL NL6817322A patent/NL6817322A/xx unknown
- 1968-12-04 AT AT1180468A patent/AT301569B/de not_active IP Right Cessation
- 1968-12-04 ZM ZM170/68A patent/ZM17068A1/xx unknown
- 1968-12-05 IL IL31228A patent/IL31228A/en unknown
- 1968-12-05 ES ES361114A patent/ES361114A1/es not_active Expired
- 1968-12-05 DK DK594468AA patent/DK126781B/da unknown
- 1968-12-06 SE SE16737/68A patent/SE346785B/xx unknown
- 1968-12-06 NO NO04900/68A patent/NO126368B/no unknown
- 1968-12-06 BE BE725104D patent/BE725104A/xx unknown
- 1968-12-06 BR BR204654/68A patent/BR6804654D0/pt unknown
- 1968-12-06 FR FR176948A patent/FR7874M/fr not_active Expired
- 1968-12-09 CH CH1833468A patent/CH534679A/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0213326A1 (de) * | 1985-08-02 | 1987-03-11 | CASSELLA Aktiengesellschaft | 2,5-Dimethylpyrrolderivative, ihre Herstellung und ihre Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| NO126368B (enrdf_load_stackoverflow) | 1973-01-29 |
| BE725104A (enrdf_load_stackoverflow) | 1969-06-06 |
| IL31228A (en) | 1972-04-27 |
| BR6804654D0 (pt) | 1973-02-13 |
| IS1807A7 (is) | 1969-01-22 |
| NL6817322A (enrdf_load_stackoverflow) | 1969-06-10 |
| ZM17068A1 (en) | 1969-06-17 |
| FR7874M (enrdf_load_stackoverflow) | 1970-04-27 |
| IE32781L (en) | 1969-06-07 |
| CH534679A (de) | 1973-03-15 |
| IL31228A0 (en) | 1969-02-27 |
| DK126781B (da) | 1973-08-20 |
| IE32781B1 (en) | 1973-11-28 |
| SE346785B (enrdf_load_stackoverflow) | 1972-07-17 |
| AT301569B (de) | 1972-09-11 |
| GB1185080A (en) | 1970-03-18 |
| ES361114A1 (es) | 1970-08-01 |
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