DE2205744A1 - Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung - Google Patents
Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellungInfo
- Publication number
- DE2205744A1 DE2205744A1 DE2205744A DE2205744A DE2205744A1 DE 2205744 A1 DE2205744 A1 DE 2205744A1 DE 2205744 A DE2205744 A DE 2205744A DE 2205744 A DE2205744 A DE 2205744A DE 2205744 A1 DE2205744 A1 DE 2205744A1
- Authority
- DE
- Germany
- Prior art keywords
- imidazolidine
- analysis
- theory
- guanidinylidene
- melting point
- 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
- -1 sulphamoyl Chemical group 0.000 claims abstract description 77
- 239000002253 acid Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
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- 102000004877 Insulin Human genes 0.000 abstract description 2
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- 230000000699 topical effect Effects 0.000 abstract description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 230000004110 gluconeogenesis Effects 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 230000003387 muscular Effects 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 239000012873 virucide Substances 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 103
- 238000002844 melting Methods 0.000 description 102
- 230000008018 melting Effects 0.000 description 102
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 80
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- 238000010626 work up procedure Methods 0.000 description 18
- 235000019270 ammonium chloride Nutrition 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 12
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 12
- BSMNBEHEFWDHJD-UHFFFAOYSA-N 2-methylpropan-1-amine;hydrochloride Chemical compound [Cl-].CC(C)C[NH3+] BSMNBEHEFWDHJD-UHFFFAOYSA-N 0.000 description 10
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- 239000008280 blood Substances 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
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- RLGVDTCKJKBXOC-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=C(Cl)C(Cl)=C1 RLGVDTCKJKBXOC-UHFFFAOYSA-N 0.000 description 6
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
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- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 4
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- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- VGBASMXDKFZLAK-UHFFFAOYSA-N 4-methylimidazolidine Chemical compound CC1CNCN1 VGBASMXDKFZLAK-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- FJLAQIPMTRVRPO-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1CCNC1=NC#N Chemical compound ClC1=CC=C(C=C1)N1CCNC1=NC#N FJLAQIPMTRVRPO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 238000010241 blood sampling Methods 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
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical group N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 229940073579 ethanolamine hydrochloride Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- XKDUZXVNQOZCFC-UHFFFAOYSA-N hexan-1-amine;hydron;chloride Chemical compound Cl.CCCCCCN XKDUZXVNQOZCFC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- DLDIDQIZPBIVNQ-UHFFFAOYSA-N hydron;2-methylpropan-2-amine;chloride Chemical compound Cl.CC(C)(C)N DLDIDQIZPBIVNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 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
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229940098465 tincture Drugs 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
- 230000003253 viricidal effect Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2205744A DE2205744A1 (de) | 1972-02-08 | 1972-02-08 | Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung |
| ES411341A ES411341A1 (es) | 1972-02-08 | 1973-02-06 | Procedimiento para la preparacion de compuestos heteroci- clicos sustituidos por un radical guanidinilideno. |
| NL7301701A NL7301701A (enExample) | 1972-02-08 | 1973-02-07 | |
| GB607273A GB1409768A (en) | 1972-02-08 | 1973-02-07 | Hererocyclic derivatives of a guanidine |
| BE795112D BE795112A (fr) | 1972-02-08 | 1973-02-07 | Nouveaux heterocycles |
| JP48015457A JPS4891068A (enExample) | 1972-02-08 | 1973-02-07 | |
| AT107173A AT319268B (de) | 1972-02-08 | 1973-02-07 | Verfahren zur Herstellung von neuen durch einen Guanidinylidenrest substituierten Imidazolidinen oder Hexahydropyrimidinen |
| AU51928/73A AU472170B2 (en) | 1972-02-08 | 1973-02-07 | Heterocyclic derivatives of guanidine |
| AT1061673A AT324351B (de) | 1972-02-08 | 1973-02-07 | Verfharen zur herstellung von neuen durch einen guanidinylidenrest substituierten imidazolidinen oder hexahydropyrimidinen und ihren physiologisch verträglichen säureadditionssalzen |
| FR7304496A FR2181714B1 (enExample) | 1972-02-08 | 1973-02-08 | |
| ES424483A ES424483A1 (es) | 1972-02-08 | 1974-03-21 | Procedimiento para la preparacion de compuestos heteroci- clicos sustituidos por un radical guanidilideno. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2205744A DE2205744A1 (de) | 1972-02-08 | 1972-02-08 | Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2205744A1 true DE2205744A1 (de) | 1973-08-09 |
Family
ID=5835294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2205744A Pending DE2205744A1 (de) | 1972-02-08 | 1972-02-08 | Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4891068A (enExample) |
| AT (2) | AT319268B (enExample) |
| AU (1) | AU472170B2 (enExample) |
| BE (1) | BE795112A (enExample) |
| DE (1) | DE2205744A1 (enExample) |
| ES (2) | ES411341A1 (enExample) |
| FR (1) | FR2181714B1 (enExample) |
| GB (1) | GB1409768A (enExample) |
| NL (1) | NL7301701A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10344002B2 (en) | 2016-09-26 | 2019-07-09 | Nusirt Sciences, Inc. | Compositions and methods for treating metabolic disorders |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4211867A (en) | 1976-03-19 | 1980-07-08 | Mcneil Laboratories, Incorporated | Nitrogen heterocyclic carboximidamide compounds |
| NZ183570A (en) * | 1976-03-19 | 1979-06-08 | Mcneilab Inc | Heterocyclic guanidine derivatives, having anti-secretory and hypogliycaemic activity |
| US4266062A (en) | 1978-09-18 | 1981-05-05 | Mcneilab, Inc. | (1-Methyl-2-pyridinylidene) derivatives of guanidine |
| US4182865A (en) * | 1978-09-18 | 1980-01-08 | Mcneil Laboratories, Inc. | Diaza-cyclic derivatives of guanidine |
| CA1201119A (en) * | 1978-09-18 | 1986-02-25 | Mcneilab, Inc. | Diaza-cyclic derivatives of guanidine |
| US4414211A (en) | 1978-09-18 | 1983-11-08 | Mcneilab, Inc. | Heterocyclic derivatives of guanidine |
| AU5263779A (en) * | 1978-11-29 | 1980-05-29 | Beecham Group Limited | Derivatives of thiazolidin-2-ylidene and oxazolidin-2-ylidene with hypoglycaemic acitivity |
| EP0018107B1 (en) | 1979-04-20 | 1982-12-22 | 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 |
| EP0020304A1 (de) * | 1979-05-29 | 1980-12-10 | Ciba-Geigy Ag | Guanidine, Verfahren zur Herstellung, pharmazeutische Präparate enthaltend solche Verbindungen und ihre Verwendung |
| EP0034002A3 (en) | 1980-01-22 | 1981-09-23 | Beecham Group Plc | Carboxamidine derivatives |
| DE102004008141A1 (de) | 2004-02-19 | 2005-09-01 | Abbott Gmbh & Co. Kg | Guanidinverbindungen und ihre Verwendung als Bindungspartner für 5-HT5-Rezeptoren |
-
1972
- 1972-02-08 DE DE2205744A patent/DE2205744A1/de active Pending
-
1973
- 1973-02-06 ES ES411341A patent/ES411341A1/es not_active Expired
- 1973-02-07 AT AT107173A patent/AT319268B/de not_active IP Right Cessation
- 1973-02-07 NL NL7301701A patent/NL7301701A/xx unknown
- 1973-02-07 BE BE795112D patent/BE795112A/xx unknown
- 1973-02-07 GB GB607273A patent/GB1409768A/en not_active Expired
- 1973-02-07 AU AU51928/73A patent/AU472170B2/en not_active Expired
- 1973-02-07 JP JP48015457A patent/JPS4891068A/ja active Pending
- 1973-02-07 AT AT1061673A patent/AT324351B/de not_active IP Right Cessation
- 1973-02-08 FR FR7304496A patent/FR2181714B1/fr not_active Expired
-
1974
- 1974-03-21 ES ES424483A patent/ES424483A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10344002B2 (en) | 2016-09-26 | 2019-07-09 | Nusirt Sciences, Inc. | Compositions and methods for treating metabolic disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| AT324351B (de) | 1975-08-25 |
| BE795112A (fr) | 1973-08-07 |
| FR2181714B1 (enExample) | 1977-07-01 |
| JPS4891068A (enExample) | 1973-11-27 |
| ES411341A1 (es) | 1976-03-16 |
| AU472170B2 (en) | 1976-05-20 |
| ES424483A1 (es) | 1976-06-16 |
| AT319268B (de) | 1974-12-10 |
| NL7301701A (enExample) | 1973-08-10 |
| AU5192873A (en) | 1974-08-08 |
| GB1409768A (en) | 1975-10-15 |
| FR2181714A1 (enExample) | 1973-12-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |