DE1445505B2 - Im phenylkern substituierte 2-phenylamino-1,3-diazacyclopentene-(2) - Google Patents
Im phenylkern substituierte 2-phenylamino-1,3-diazacyclopentene-(2)Info
- Publication number
- DE1445505B2 DE1445505B2 DE1963B0073766 DEB0073766A DE1445505B2 DE 1445505 B2 DE1445505 B2 DE 1445505B2 DE 1963B0073766 DE1963B0073766 DE 1963B0073766 DE B0073766 A DEB0073766 A DE B0073766A DE 1445505 B2 DE1445505 B2 DE 1445505B2
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- methylphenyl
- diazacyclopentene
- amino
- acid
- 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.)
- Granted
Links
- -1 PHENYL CORE Chemical group 0.000 title description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 16
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 13
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 229940099112 cornstarch Drugs 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical class [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- UAISVUGQLKXPFF-UHFFFAOYSA-N 2,4-dichloro-6-methylaniline Chemical compound CC1=CC(Cl)=CC(Cl)=C1N UAISVUGQLKXPFF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 241000011102 Thera Species 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000005923 long-lasting effect Effects 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000004617 sleep duration Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL123037D NL123037C (enrdf_load_stackoverflow) | 1963-10-04 | ||
| DE1963B0073766 DE1445505B2 (de) | 1963-10-04 | 1963-10-04 | Im phenylkern substituierte 2-phenylamino-1,3-diazacyclopentene-(2) |
| US327806A US3236857A (en) | 1961-10-09 | 1963-12-03 | 2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products |
| DE19641445538 DE1445538A1 (de) | 1963-10-04 | 1964-07-31 | Verfahren zur Herstellung neuer substituierter Phenylamino-1,3-diazacyclopentene-(2) |
| CH1189367A CH451172A (de) | 1963-10-04 | 1964-09-14 | Verfahren zur Herstellung neuer substituierter Phenylamino-1,3-diazacyclopentene-(2) |
| CH1193264A CH437316A (de) | 1963-10-04 | 1964-09-14 | Verfahren zur Herstellung von substituierten Phenyl-amino-1,3-diazacyclopenten-(2)-Verbindungen |
| CH1193164A CH451169A (de) | 1963-10-04 | 1964-09-14 | Verfahren zur Herstellung neuer substituierter Phenylamino-1,3-diazacyclopentene-(2) |
| SE1110764A SE313310B (enrdf_load_stackoverflow) | 1963-10-04 | 1964-09-16 | |
| SE1071068A SE353721B (enrdf_load_stackoverflow) | 1963-10-04 | 1964-09-16 | |
| FI201764A FI44913C (fi) | 1963-10-04 | 1964-09-23 | Menetelmä uusien substituoitujen fenyyliamino-1,3-diatsasyklopenteenien-(2) valmistamiseksi, joilla on verenpainetta alentava ja rauhoittava vaikutus |
| GB39420/64A GB1034938A (en) | 1963-10-04 | 1964-09-28 | 2-phenylamino-1,3-diazacyclopent-2-enes |
| FR990056A FR3968M (enrdf_load_stackoverflow) | 1963-10-04 | 1964-10-01 | |
| FR990057A FR1448765A (fr) | 1963-10-04 | 1964-10-01 | Procédé pour fabriquer des nouveaux phénylamino-1, 3-diazacyclopentènes-(2)-substitués |
| BR16314264A BR6463142D0 (pt) | 1963-10-04 | 1964-10-02 | Processo para a obtencao de novos fenilamino-1,3- diazacicativo |
| BE653933D BE653933A (enrdf_load_stackoverflow) | 1963-10-04 | 1964-10-02 | |
| DK486964A DK108364C (da) | 1963-10-04 | 1964-10-02 | Fremgangsmåde til fremstilling af substituerede phenylamino-1,3-diazacyclopentener-(2)-, eller syreadditionssalte heraf. |
| NL6411516A NL6411516A (enrdf_load_stackoverflow) | 1961-10-09 | 1964-10-02 | |
| IL2218664A IL22186A (en) | 1963-10-04 | 1964-10-04 | Phenylamino-1,3-diazacyclopentenes,process for their preparation and compositions containing them |
| DK482765A DK117000B (da) | 1963-10-04 | 1965-09-20 | Fremgangsmåde til fremstilling af substituerede phenylamino-1,3-diazacyclopentener-(2) eller syreadditionssalte heraf. |
| US515479A US3454701A (en) | 1961-10-09 | 1965-12-21 | 2 - (phenyl - amino) - 1,3 - diazacyclopentene - (2) substitution products for reducing blood pressure |
| FI260071A FI49614C (fi) | 1963-10-04 | 1971-09-17 | Menetelmä substituoitujen fenyyliamino-1,3-diatsasyklopenteenien-(2) v almistamiseksi, joilla on verisuonia supistava, verenpainetta alentava ja rauhoittava vaikutus. |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1963B0073766 DE1445505B2 (de) | 1963-10-04 | 1963-10-04 | Im phenylkern substituierte 2-phenylamino-1,3-diazacyclopentene-(2) |
| DEB0077922 | 1964-07-31 | ||
| DEB0077921 | 1964-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1445505A1 DE1445505A1 (de) | 1969-10-02 |
| DE1445505B2 true DE1445505B2 (de) | 1976-12-16 |
Family
ID=27209240
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963B0073766 Granted DE1445505B2 (de) | 1961-10-09 | 1963-10-04 | Im phenylkern substituierte 2-phenylamino-1,3-diazacyclopentene-(2) |
| DE19641445538 Pending DE1445538A1 (de) | 1963-10-04 | 1964-07-31 | Verfahren zur Herstellung neuer substituierter Phenylamino-1,3-diazacyclopentene-(2) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445538 Pending DE1445538A1 (de) | 1963-10-04 | 1964-07-31 | Verfahren zur Herstellung neuer substituierter Phenylamino-1,3-diazacyclopentene-(2) |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE653933A (enrdf_load_stackoverflow) |
| BR (1) | BR6463142D0 (enrdf_load_stackoverflow) |
| CH (3) | CH437316A (enrdf_load_stackoverflow) |
| DE (2) | DE1445505B2 (enrdf_load_stackoverflow) |
| DK (2) | DK108364C (enrdf_load_stackoverflow) |
| FI (2) | FI44913C (enrdf_load_stackoverflow) |
| FR (2) | FR3968M (enrdf_load_stackoverflow) |
| GB (1) | GB1034938A (enrdf_load_stackoverflow) |
| IL (1) | IL22186A (enrdf_load_stackoverflow) |
| NL (1) | NL123037C (enrdf_load_stackoverflow) |
| SE (2) | SE353721B (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545628A1 (de) * | 1965-10-01 | 1970-06-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von blutdrucksenkend und sedativ wirksamen Derivaten des 2-(2-Halogenanilino)-1,3-diazacyclopentens-(2) |
| BE754832A (fr) * | 1969-08-14 | 1971-02-15 | Beecham Group Ltd | Iminazolines |
| US4125620A (en) | 1974-10-01 | 1978-11-14 | Boehringer Ingelheim Gmbh | 2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof |
| MTP837B (en) | 1977-11-07 | 1979-10-22 | Hoffman La Roche And Co Aktien | Derivatives 2 finino-imidazolidire |
| DE2806811A1 (de) * | 1978-02-17 | 1979-08-23 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylimino- imidazolidine, deren saeureadditionssalze, diese enthaltene arzneimittel und verfahren zur herstellung derselben |
| DE2854659A1 (de) * | 1978-12-18 | 1980-07-10 | Boehringer Sohn Ingelheim | Neue 3,4-disubstituierte 2-phenylimino-imidazolidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| CA1175434A (en) | 1980-09-10 | 1984-10-02 | Hoffmann-La Roche Limited | ¬(2-phenylamino-1-imidazolidinyloxy)methyl| pyridine 1-oxide derivatives |
| US4444782A (en) * | 1982-12-23 | 1984-04-24 | Smithkline Beckman Corporation | 2(4-tert.-Butyl-2,6-dichlorophenyl-imino)imidazolidine and use as an anti-hypertension agent |
-
0
- NL NL123037D patent/NL123037C/xx active
-
1963
- 1963-10-04 DE DE1963B0073766 patent/DE1445505B2/de active Granted
-
1964
- 1964-07-31 DE DE19641445538 patent/DE1445538A1/de active Pending
- 1964-09-14 CH CH1193264A patent/CH437316A/de unknown
- 1964-09-14 CH CH1193164A patent/CH451169A/de unknown
- 1964-09-14 CH CH1189367A patent/CH451172A/de unknown
- 1964-09-16 SE SE1071068A patent/SE353721B/xx unknown
- 1964-09-16 SE SE1110764A patent/SE313310B/xx unknown
- 1964-09-23 FI FI201764A patent/FI44913C/fi active
- 1964-09-28 GB GB39420/64A patent/GB1034938A/en not_active Expired
- 1964-10-01 FR FR990056A patent/FR3968M/fr not_active Expired
- 1964-10-01 FR FR990057A patent/FR1448765A/fr not_active Expired
- 1964-10-02 BR BR16314264A patent/BR6463142D0/pt unknown
- 1964-10-02 DK DK486964A patent/DK108364C/da active
- 1964-10-02 BE BE653933D patent/BE653933A/xx unknown
- 1964-10-04 IL IL2218664A patent/IL22186A/xx unknown
-
1965
- 1965-09-20 DK DK482765A patent/DK117000B/da unknown
-
1971
- 1971-09-17 FI FI260071A patent/FI49614C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| IL22186A (en) | 1968-06-20 |
| CH451172A (de) | 1968-05-15 |
| CH451169A (de) | 1968-05-15 |
| FI44913B (enrdf_load_stackoverflow) | 1971-11-01 |
| FI49614B (enrdf_load_stackoverflow) | 1975-04-30 |
| FR3968M (enrdf_load_stackoverflow) | 1966-02-28 |
| GB1034938A (en) | 1966-07-06 |
| DE1445538A1 (de) | 1969-02-20 |
| FI44913C (fi) | 1972-02-10 |
| NL123037C (enrdf_load_stackoverflow) | |
| FR1448765A (fr) | 1966-03-18 |
| BR6463142D0 (pt) | 1973-07-19 |
| CH437316A (de) | 1967-06-15 |
| SE313310B (enrdf_load_stackoverflow) | 1969-08-11 |
| DE1445505A1 (de) | 1969-10-02 |
| BE653933A (enrdf_load_stackoverflow) | 1965-04-02 |
| DK117000B (da) | 1970-03-09 |
| SE353721B (enrdf_load_stackoverflow) | 1973-02-12 |
| DK108364C (da) | 1967-11-27 |
| FI49614C (fi) | 1975-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |