DE2622639A1 - 2,4-diamino-5-brom-6-chlor-pyrimidinderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel - Google Patents
2,4-diamino-5-brom-6-chlor-pyrimidinderivate, verfahren zu deren herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2622639A1 DE2622639A1 DE19762622639 DE2622639A DE2622639A1 DE 2622639 A1 DE2622639 A1 DE 2622639A1 DE 19762622639 DE19762622639 DE 19762622639 DE 2622639 A DE2622639 A DE 2622639A DE 2622639 A1 DE2622639 A1 DE 2622639A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- groups
- solution
- bromine
- effect
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 29
- 230000000694 effects Effects 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkali metal hypobromite Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003420 antiserotonin agent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 230000000794 anti-serotonin Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000000767 anti-ulcer Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 230000003457 anti-vomiting effect Effects 0.000 claims description 3
- 150000002926 oxygen Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 230000002082 anti-convulsion Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000000506 psychotropic effect Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 208000007101 Muscle Cramp Diseases 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 5
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- REENKIULWYZNPE-UHFFFAOYSA-N 5-bromo-6-chloropyrimidine-2,4-diamine Chemical class NC1=NC(N)=C(Br)C(Cl)=N1 REENKIULWYZNPE-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000003474 anti-emetic effect Effects 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 239000002111 antiemetic agent Substances 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003170 musculotropic effect Effects 0.000 description 2
- 230000002276 neurotropic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000004089 psychotropic agent Substances 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NZRAIMUNWMVSMC-UHFFFAOYSA-N 1-(4-chloro-5-methylsulfanylpyrimidin-2-yl)-n,4-dimethylpiperazin-2-amine Chemical compound CNC1CN(C)CCN1C1=NC=C(SC)C(Cl)=N1 NZRAIMUNWMVSMC-UHFFFAOYSA-N 0.000 description 1
- DDWBEROMBZXLNB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylsulfanylpyrimidine Chemical compound CSC1=C(Cl)N=C(Cl)N=C1Cl DDWBEROMBZXLNB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- UMMYPDFDLDVDCZ-UHFFFAOYSA-N 4-chloro-6-(4-methylpiperazin-1-yl)-5-methylsulfanyl-n-propan-2-ylpyrimidin-2-amine Chemical compound CSC1=C(Cl)N=C(NC(C)C)N=C1N1CCN(C)CC1 UMMYPDFDLDVDCZ-UHFFFAOYSA-N 0.000 description 1
- SICCNKVSVFOZFM-UHFFFAOYSA-N 5-bromo-4,6-dichloro-N-methylpyrimidin-2-amine Chemical compound CNC1=NC(Cl)=C(Br)C(Cl)=N1 SICCNKVSVFOZFM-UHFFFAOYSA-N 0.000 description 1
- LAUORAFVFXRKDL-UHFFFAOYSA-N 5-bromo-4,6-dichloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=C(Br)C(Cl)=N1 LAUORAFVFXRKDL-UHFFFAOYSA-N 0.000 description 1
- IBMKUYMVNFUNOW-UHFFFAOYSA-N 5-methylsulfanylpyrimidine Chemical class CSC1=CN=CN=C1 IBMKUYMVNFUNOW-UHFFFAOYSA-N 0.000 description 1
- QQRJUWIHLNBDQF-UHFFFAOYSA-N 6-chloro-5-methylsulfanylpyrimidine-2,4-diamine Chemical class CSC1=C(N)N=C(N)N=C1Cl QQRJUWIHLNBDQF-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229910020314 ClBr Inorganic materials 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001071864 Lethrinus laticaudis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100460719 Mus musculus Noto gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
Classifications
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7516088A FR2311776A1 (fr) | 1975-05-23 | 1975-05-23 | Diamino-2,4 bromo-5 chloro-6 pyrimidines et procede pour leur preparation |
| FR7516089A FR2311547A1 (fr) | 1975-05-23 | 1975-05-23 | Nouveau medicament derive de pyrimidine a proprietes anti-ulcereuses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2622639A1 true DE2622639A1 (de) | 1976-12-09 |
Family
ID=26218882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762622639 Ceased DE2622639A1 (de) | 1975-05-23 | 1976-05-20 | 2,4-diamino-5-brom-6-chlor-pyrimidinderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel |
Country Status (10)
| Country | Link |
|---|---|
| CA (1) | CA1068270A (enrdf_load_stackoverflow) |
| CH (1) | CH602663A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2622639A1 (enrdf_load_stackoverflow) |
| ES (1) | ES448168A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1554227A (enrdf_load_stackoverflow) |
| IT (1) | IT1070500B (enrdf_load_stackoverflow) |
| LU (1) | LU75002A1 (enrdf_load_stackoverflow) |
| MX (1) | MX3527E (enrdf_load_stackoverflow) |
| NL (1) | NL7605319A (enrdf_load_stackoverflow) |
| PT (1) | PT65122B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0111440A1 (en) * | 1982-10-15 | 1984-06-20 | Ciba-Geigy Ag | 2-Aminopyrimidines, their production and use |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2006145A1 (de) * | 1969-02-14 | 1970-10-29 | Sandoz Ag, Basel (Schweiz) | Herbizide Mittel |
| DE2307536A1 (de) * | 1972-03-01 | 1973-09-13 | Ugine Kuhlmann | Neue pyrimidinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE2342880A1 (de) * | 1973-07-06 | 1975-01-30 | Ugine Kuhlmann | Piperazin-pyrimidine, verfahren zu ihrer herstellung und ihre verwendung |
-
1976
- 1976-05-19 CH CH627176A patent/CH602663A5/xx not_active IP Right Cessation
- 1976-05-19 NL NL7605319A patent/NL7605319A/xx not_active Application Discontinuation
- 1976-05-20 DE DE19762622639 patent/DE2622639A1/de not_active Ceased
- 1976-05-21 GB GB2100276A patent/GB1554227A/en not_active Expired
- 1976-05-21 IT IT6824376A patent/IT1070500B/it active
- 1976-05-21 PT PT6512276A patent/PT65122B/pt unknown
- 1976-05-21 ES ES448168A patent/ES448168A1/es not_active Expired
- 1976-05-21 CA CA253,151A patent/CA1068270A/fr not_active Expired
- 1976-05-21 LU LU75002A patent/LU75002A1/xx unknown
- 1976-05-31 MX MX10034476U patent/MX3527E/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2006145A1 (de) * | 1969-02-14 | 1970-10-29 | Sandoz Ag, Basel (Schweiz) | Herbizide Mittel |
| DE2307536A1 (de) * | 1972-03-01 | 1973-09-13 | Ugine Kuhlmann | Neue pyrimidinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE2342880A1 (de) * | 1973-07-06 | 1975-01-30 | Ugine Kuhlmann | Piperazin-pyrimidine, verfahren zu ihrer herstellung und ihre verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| ES448168A1 (es) | 1977-12-01 |
| GB1554227A (en) | 1979-10-17 |
| MX3527E (es) | 1981-01-27 |
| PT65122B (fr) | 1977-10-11 |
| NL7605319A (nl) | 1976-11-25 |
| CA1068270A (fr) | 1979-12-18 |
| PT65122A (fr) | 1976-06-01 |
| CH602663A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| LU75002A1 (enrdf_load_stackoverflow) | 1977-01-19 |
| IT1070500B (it) | 1985-03-29 |
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