GB1573532A - Heterocyclic derivatives of guanidine - Google Patents
Heterocyclic derivatives of guanidine Download PDFInfo
- Publication number
- GB1573532A GB1573532A GB10988/77A GB1098877A GB1573532A GB 1573532 A GB1573532 A GB 1573532A GB 10988/77 A GB10988/77 A GB 10988/77A GB 1098877 A GB1098877 A GB 1098877A GB 1573532 A GB1573532 A GB 1573532A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- pyrrolidinylidene
- formula
- group
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title claims description 28
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title claims description 16
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 10
- -1 Heterocyclic guanidine derivatives Chemical class 0.000 claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 39
- 239000012458 free base Substances 0.000 claims abstract description 37
- 238000010992 reflux Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- UFJFKQGRZLHOBO-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-phenylpyrrolidine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCCC1)=NC1=CC=CC=C1 UFJFKQGRZLHOBO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 claims description 4
- RXTDULLEVFGZRI-UHFFFAOYSA-N methyl n-(1-methylpyrrolidin-2-ylidene)-n'-phenylcarbamimidothioate;hydroiodide Chemical compound I.C=1C=CC=CC=1N=C(SC)N=C1CCCN1C RXTDULLEVFGZRI-UHFFFAOYSA-N 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- OPPLDIXFHYTSSR-GLECISQGSA-N (ne)-n-(1-methylpyrrolidin-2-ylidene)-n'-phenylmorpholine-4-carboximidamide Chemical compound CN1CCC\C1=N/C(N1CCOCC1)=NC1=CC=CC=C1 OPPLDIXFHYTSSR-GLECISQGSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- MRQLEWVLRPTNSW-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-phenylthiomorpholine-4-carboximidamide Chemical compound CN1CCCC1=NC(N1CCSCC1)=NC1=CC=CC=C1 MRQLEWVLRPTNSW-UHFFFAOYSA-N 0.000 claims 2
- PNRQSQULNGFBNT-UHFFFAOYSA-N 1,1-diethyl-3-(1-methylpyrrolidin-2-ylidene)-2-phenylguanidine Chemical compound C=1C=CC=CC=1N=C(N(CC)CC)N=C1CCCN1C PNRQSQULNGFBNT-UHFFFAOYSA-N 0.000 claims 1
- QQRMWMRSWUAHPU-UHFFFAOYSA-N 1-cyclohexyl-1-methyl-3-(1-methylpyrrolidin-2-ylidene)-2-naphthalen-1-ylguanidine Chemical compound C1CCN(C)C1=NC(=NC=1C2=CC=CC=C2C=CC=1)N(C)C1CCCCC1 QQRMWMRSWUAHPU-UHFFFAOYSA-N 0.000 claims 1
- DJIWEJWHFOJHSU-UHFFFAOYSA-N 1-cyclopentyl-1-methyl-3-(1-methylpyrrolidin-2-ylidene)-2-phenylguanidine Chemical compound C1CCN(C)C1=NC(=NC=1C=CC=CC=1)N(C)C1CCCC1 DJIWEJWHFOJHSU-UHFFFAOYSA-N 0.000 claims 1
- NEJFMNLZTXMLKM-UHFFFAOYSA-N 4-methyl-n-(1-methylpyrrolidin-2-ylidene)-n'-phenylpiperazine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCN(C)CC1)=NC1=CC=CC=C1 NEJFMNLZTXMLKM-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- AUISAPOBZIEJFM-UHFFFAOYSA-N n'-(1,3-benzodioxol-5-yl)-n-(1-methylpyrrolidin-2-ylidene)piperidine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCCCC1)=NC1=CC=C(OCO2)C2=C1 AUISAPOBZIEJFM-UHFFFAOYSA-N 0.000 claims 1
- CDPVHAXCHWVARH-UHFFFAOYSA-N n'-(3-chlorophenyl)morpholine-4-carboximidamide Chemical compound C1COCCN1C(N)=NC1=CC=CC(Cl)=C1 CDPVHAXCHWVARH-UHFFFAOYSA-N 0.000 claims 1
- VYECSZSYEXXESU-UHFFFAOYSA-N n'-(4-methoxyphenyl)-n-(1-methylpyrrolidin-2-ylidene)pyrrolidine-1-carboximidamide Chemical compound C1=CC(OC)=CC=C1N=C(N1CCCC1)N=C1N(C)CCC1 VYECSZSYEXXESU-UHFFFAOYSA-N 0.000 claims 1
- DVMYSDBVFAXGHO-UHFFFAOYSA-N n'-(4-methylphenyl)pyrrolidine-1-carboximidamide Chemical compound C1=CC(C)=CC=C1NC(=N)N1CCCC1 DVMYSDBVFAXGHO-UHFFFAOYSA-N 0.000 claims 1
- WFOGJDBFYKHGII-UHFFFAOYSA-N n-(1,5-dimethylpyrrolidin-2-ylidene)-n'-phenylpyrrolidine-1-carboximidamide Chemical compound CN1C(C)CCC1=NC(N1CCCC1)=NC1=CC=CC=C1 WFOGJDBFYKHGII-UHFFFAOYSA-N 0.000 claims 1
- ZUYSAPAZRNTDIT-UHFFFAOYSA-N n-(1-benzylpyrrolidin-2-ylidene)-n'-phenylmorpholine-4-carboximidamide Chemical compound C=1C=CC=CC=1CN1CCCC1=NC(N1CCOCC1)=NC1=CC=CC=C1 ZUYSAPAZRNTDIT-UHFFFAOYSA-N 0.000 claims 1
- REJALTGYTMJHKN-UHFFFAOYSA-N n-(1-ethylpyrrolidin-2-ylidene)-n'-phenylpyrrolidine-1-carboximidamide Chemical compound CCN1CCCC1=NC(N1CCCC1)=NC1=CC=CC=C1 REJALTGYTMJHKN-UHFFFAOYSA-N 0.000 claims 1
- AOAJXWHLTGXYJQ-UHFFFAOYSA-N n-(1-methylazepan-2-ylidene)-n'-phenylpyrrolidine-1-carboximidamide Chemical compound CN1CCCCCC1=NC(N1CCCC1)=NC1=CC=CC=C1 AOAJXWHLTGXYJQ-UHFFFAOYSA-N 0.000 claims 1
- HLOCYGDRSJCYHY-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n',4-diphenylpiperazine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCN(CC1)C=1C=CC=CC=1)=NC1=CC=CC=C1 HLOCYGDRSJCYHY-UHFFFAOYSA-N 0.000 claims 1
- KILSOTHRLVCGDZ-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-(4-methylsulfanylphenyl)morpholine-4-carboximidamide Chemical compound C1=CC(SC)=CC=C1N=C(N1CCOCC1)N=C1N(C)CCC1 KILSOTHRLVCGDZ-UHFFFAOYSA-N 0.000 claims 1
- MNMUKGISUINVGO-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-naphthalen-2-ylpyrrolidine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCCC1)=NC1=CC=C(C=CC=C2)C2=C1 MNMUKGISUINVGO-UHFFFAOYSA-N 0.000 claims 1
- XXWKTPMEZDMEOD-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-phenylpiperidine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCCCC1)=NC1=CC=CC=C1 XXWKTPMEZDMEOD-UHFFFAOYSA-N 0.000 claims 1
- NLEBTKAEIJFDJF-UHFFFAOYSA-N n-[1-(2-hydroxyethyl)pyrrolidin-2-ylidene]-n'-phenylmorpholine-4-carboximidamide Chemical compound OCCN1CCCC1=NC(N1CCOCC1)=NC1=CC=CC=C1 NLEBTKAEIJFDJF-UHFFFAOYSA-N 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 9
- 239000008280 blood Substances 0.000 abstract description 8
- 210000004369 blood Anatomy 0.000 abstract description 8
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract description 4
- 210000004051 gastric juice Anatomy 0.000 abstract description 3
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000005323 carbonate salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- JUFUUHNYUZQEKT-UHFFFAOYSA-N cyclohexylsulfamic acid 1-(2-iminopyrrolidin-1-yl)ethanol Chemical compound C1(CCCCC1)NS(=O)(=O)O.OC(C)N1C(CCC1)=N JUFUUHNYUZQEKT-UHFFFAOYSA-N 0.000 description 1
- MHGNMFDITHQPFG-UHFFFAOYSA-N cyclohexylsulfamic acid;1-methylazepan-2-imine Chemical compound CN1CCCCCC1=N.OS(=O)(=O)NC1CCCCC1 MHGNMFDITHQPFG-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- VQHPEFRLPAMDOL-UHFFFAOYSA-N dichloromethanimine Chemical class ClC(Cl)=N VQHPEFRLPAMDOL-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000004341 endo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- GKRYGIRXXGHASA-UHFFFAOYSA-N ethyl n-(1,3-benzodioxol-5-ylcarbamothioyl)carbamate Chemical compound CCOC(=O)NC(=S)NC1=CC=C2OCOC2=C1 GKRYGIRXXGHASA-UHFFFAOYSA-N 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical group CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical class I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000004694 iodide salts Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- VCYDMRNMHRTRFE-UHFFFAOYSA-N methyl n'-(4-methylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(N)=NC1=CC=C(C)C=C1 VCYDMRNMHRTRFE-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ARBAONBMFHRZGV-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-(4-methylsulfinylphenyl)morpholine-4-carboximidamide Chemical compound CN1CCCC1=NC(N1CCOCC1)=NC1=CC=C(S(C)=O)C=C1 ARBAONBMFHRZGV-UHFFFAOYSA-N 0.000 description 1
- MVUDBNMUQYRCQK-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-(4-nitrophenyl)pyrrolidine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCCC1)=NC1=CC=C([N+]([O-])=O)C=C1 MVUDBNMUQYRCQK-UHFFFAOYSA-N 0.000 description 1
- JITSRGDIBDNJAX-UHFFFAOYSA-N n-(1-methylpyrrolidin-2-ylidene)-n'-(4-phenylmethoxyphenyl)pyrrolidine-1-carboximidamide Chemical compound CN1CCCC1=NC(N1CCCC1)=NC(C=C1)=CC=C1OCC1=CC=CC=C1 JITSRGDIBDNJAX-UHFFFAOYSA-N 0.000 description 1
- AWENPGVEOVOLRY-UHFFFAOYSA-N n-[(4-methylsulfanylphenyl)carbamothioyl]benzamide Chemical compound C1=CC(SC)=CC=C1NC(=S)NC(=O)C1=CC=CC=C1 AWENPGVEOVOLRY-UHFFFAOYSA-N 0.000 description 1
- USEMRPYUFJNFQN-UHFFFAOYSA-N n-cyclohexyl-2-(3,5-dimethylpyrazol-1-yl)-6-methylpyrimidin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(C)=CC(NC2CCCCC2)=N1 USEMRPYUFJNFQN-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940127066 new oral anticoagluant drug Drugs 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000005485 noradamantyl group Chemical group 0.000 description 1
- 229940089787 novel oral anticoagluant drug Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- 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
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US66838676A | 1976-03-19 | 1976-03-19 | |
US75258876A | 1976-12-20 | 1976-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1573532A true GB1573532A (en) | 1980-08-28 |
Family
ID=27099888
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10988/77A Expired GB1573532A (en) | 1976-03-19 | 1977-03-15 | Heterocyclic derivatives of guanidine |
Country Status (21)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4355004A (en) | 1979-11-10 | 1982-10-19 | Beecham Group Limited | Benzimidazoline derivatives and pharmaceutical compositions containing them |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995009619A2 (en) * | 1993-10-04 | 1995-04-13 | The Wellcome Foundation Limited | Substituted urea and isothiourea derivatives as no synthase inhibitors |
US4101659A (en) * | 1977-08-29 | 1978-07-18 | Mcneil Laboratories, Incorporated | Benzhydryl guanidines |
ZA793186B (en) * | 1978-07-06 | 1981-02-25 | Duphar Int Res | New urea and thiourea compounds, method of preparing the new compounds, as well as insecticidal compositions on the basis of these compounds |
DE3061396D1 (en) * | 1979-04-20 | 1983-01-27 | Beecham Group Plc | Oxazoline and thiazoline derivatives, processes for their preparation and pharmaceutical compositions containing them |
JPS55160764A (en) * | 1979-05-29 | 1980-12-13 | Ciba Geigy Ag | Guanidine* its manufacture and pharmaceutic medicine containing same |
JPH06198992A (ja) * | 1992-11-30 | 1994-07-19 | Shinko Seisakusho Co Ltd | 紙葉類搬送装置 |
ATE180255T1 (de) * | 1993-03-23 | 1999-06-15 | Astra Ab | Guanidinderivate mit therapeutischer wirkung |
US6297276B1 (en) | 1993-10-04 | 2001-10-02 | Glaxosmithkline | Substituted urea and isothiourea derivatives as no synthase inhibitors |
US6225305B1 (en) | 1993-10-04 | 2001-05-01 | Glaxo Wellcome Inc. | Substituted urea and isothiorea derivatives as no synthase inhibitors |
US6090846A (en) * | 1994-06-01 | 2000-07-18 | Glaxo Wellcome Inc. | Substituted urea and isothiourea derivatives as no synthase inhibitors |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2205744A1 (de) * | 1972-02-08 | 1973-08-09 | Thomae Gmbh Dr K | Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung |
CH578539A5 (enrdf_load_stackoverflow) * | 1972-03-17 | 1976-08-13 | Mcneilab Inc | |
US3803170A (en) * | 1972-08-11 | 1974-04-09 | Richardson Merrell Inc | 2-((1-benzylcyclopentyl)imino)pyrrolidine |
-
1977
- 1977-03-10 NZ NZ183570A patent/NZ183570A/xx unknown
- 1977-03-14 GR GR52986A patent/GR60780B/el unknown
- 1977-03-15 GB GB10988/77A patent/GB1573532A/en not_active Expired
- 1977-03-17 DE DE19772711757 patent/DE2711757A1/de not_active Ceased
- 1977-03-17 NO NO770959A patent/NO148524C/no unknown
- 1977-03-17 AU AU23351/77A patent/AU517804B2/en not_active Expired
- 1977-03-18 NL NL7703011A patent/NL7703011A/xx not_active Application Discontinuation
- 1977-03-18 SE SE7703114A patent/SE423628B/xx not_active IP Right Cessation
- 1977-03-18 PH PH19565A patent/PH16561A/en unknown
- 1977-03-18 FI FI770864A patent/FI65243C/fi not_active IP Right Cessation
- 1977-03-18 FR FR7708229A patent/FR2361366A1/fr active Granted
- 1977-03-18 DK DK119477A patent/DK119477A/da not_active Application Discontinuation
- 1977-03-18 JP JP2941177A patent/JPS52136168A/ja active Granted
- 1977-03-18 IL IL51694A patent/IL51694A/xx unknown
- 1977-03-18 ES ES457010A patent/ES457010A1/es not_active Expired
- 1977-03-18 CA CA274,239A patent/CA1100494A/en not_active Expired
- 1977-03-18 AT AT190677A patent/AT356669B/de not_active IP Right Cessation
- 1977-03-18 IE IE584/77A patent/IE44792B1/en unknown
- 1977-03-18 RO RO7789709A patent/RO71209A/ro unknown
- 1977-03-18 CH CH344877A patent/CH635073A5/de not_active IP Right Cessation
- 1977-03-21 DD DD7700197955A patent/DD130242A5/xx unknown
-
1981
- 1981-03-13 CH CH175081A patent/CH632994A5/de not_active IP Right Cessation
-
1982
- 1982-04-02 CH CH206282A patent/CH636084A5/de not_active IP Right Cessation
- 1982-04-02 CH CH206182A patent/CH634557A5/de not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4355004A (en) | 1979-11-10 | 1982-10-19 | Beecham Group Limited | Benzimidazoline derivatives and pharmaceutical compositions containing them |
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Legal Events
Date | Code | Title | Description |
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PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |