GB1113262A - Improvements in or relating to substituted pyrazines and the manufacture thereof - Google Patents
Improvements in or relating to substituted pyrazines and the manufacture thereofInfo
- Publication number
- GB1113262A GB1113262A GB25938/65A GB2593865A GB1113262A GB 1113262 A GB1113262 A GB 1113262A GB 25938/65 A GB25938/65 A GB 25938/65A GB 2593865 A GB2593865 A GB 2593865A GB 1113262 A GB1113262 A GB 1113262A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- carbamoyl
- salts
- acid
- pyrazine
- 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
- 150000003216 pyrazines Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 4
- -1 pomoate Chemical class 0.000 abstract 4
- 229910002651 NO3 Inorganic materials 0.000 abstract 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Chemical class 0.000 abstract 2
- 239000002184 metal Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Chemical class 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- VHRSUDSXCMQTMA-UHFFFAOYSA-N 11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound CC12C=CC(=O)C=C1C(C)CC1C2C(O)CC2(C)C(O)(C(=O)CO)CCC21 VHRSUDSXCMQTMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000001934 2,5-dimethylpyrazine Substances 0.000 abstract 1
- WSMQKESQZFQMFW-UHFFFAOYSA-N 5-methyl-pyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1 WSMQKESQZFQMFW-UHFFFAOYSA-N 0.000 abstract 1
- QMNAQPMXDMLOLD-UHFFFAOYSA-N 6-methyl-4-oxo-5,6-dihydrothieno[2,3-b]thiopyran-2-sulfonamide Chemical compound S1C(C)CC(=O)C2=C1SC(S(N)(=O)=O)=C2 QMNAQPMXDMLOLD-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- MQGBKWWRPALWQN-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)O)C.CC1=NC=C(N=C1)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.CC1=NC=C(N=C1)C MQGBKWWRPALWQN-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical class [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- RTPLCYNAEQZNQR-UHFFFAOYSA-N Cl.CC1=NC=C(N=C1)C Chemical compound Cl.CC1=NC=C(N=C1)C RTPLCYNAEQZNQR-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 102000004877 Insulin Human genes 0.000 abstract 1
- 108090001061 Insulin Proteins 0.000 abstract 1
- 229930182558 Sterol Natural products 0.000 abstract 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000003098 androgen Substances 0.000 abstract 1
- 229940030486 androgens Drugs 0.000 abstract 1
- 229940124332 anorexigenic agent Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 229940127219 anticoagulant drug Drugs 0.000 abstract 1
- 239000002830 appetite depressant Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000002327 cardiovascular agent Substances 0.000 abstract 1
- 229940125692 cardiovascular agent Drugs 0.000 abstract 1
- 150000001805 chlorine compounds Chemical group 0.000 abstract 1
- 229960001761 chlorpropamide Drugs 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 229940030606 diuretics Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940011871 estrogen Drugs 0.000 abstract 1
- 239000000262 estrogen Substances 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 229960000890 hydrocortisone Drugs 0.000 abstract 1
- 229940125396 insulin Drugs 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- YDTFRJLNMPSCFM-YDALLXLXSA-M levothyroxine sodium anhydrous Chemical compound [Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 YDTFRJLNMPSCFM-YDALLXLXSA-M 0.000 abstract 1
- 239000003912 lipotropic agent Substances 0.000 abstract 1
- 229940040504 lipotropic agent Drugs 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 229960001753 phenformin hydrochloride Drugs 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 229960005205 prednisolone Drugs 0.000 abstract 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 abstract 1
- YDTFRJLNMPSCFM-UTONKHPSSA-M sodium;(2r)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate Chemical compound [Na+].IC1=CC(C[C@@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 YDTFRJLNMPSCFM-UTONKHPSSA-M 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003432 sterols Chemical class 0.000 abstract 1
- 235000003702 sterols Nutrition 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical class [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 229960005371 tolbutamide Drugs 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 229940035722 triiodothyronine Drugs 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 1
- 239000011782 vitamin Substances 0.000 abstract 1
- 229940088594 vitamin Drugs 0.000 abstract 1
- 229930003231 vitamin Natural products 0.000 abstract 1
- 235000013343 vitamin Nutrition 0.000 abstract 1
- 235000012431 wafers Nutrition 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Novel mono-alkyl substituted and dialkyl substituted 2-alkyl-5-carbamoyl pyrazines are prepared by reacting a 2-alkyl-5-carboxy-pyrazine with a monoalkyl amine or dialkyl amine respectively where the alkyl groups contain 1 to 4 C atoms. The invention also includes 2,5-dimethyl pyrazine p-toluene sulphonate and its preparation by reacting 2,5-dimethyl pyrazine with p-toluene-sulphonic acid, and the salts of the above carbamoyl derivatives. The compounds have therapeutic properties. The preparation of 2,5-dimethyl pyrazine hydrochloride and nitrate from the corresponding acids is also described. Specified salts of the main carbamoyl derivatives are the hydrochloride, cyclohexylsulphamate, sulphate, acetate, nitrate, phosphate, citrate, maleate, tartrate, succinate, pomoate, p-toluene sulphonate, benzenesulphonate, alkali metal salts, alkaline earth metal salts, amine salts, ammonium salts, and metal salt complexes wherein the metal salt is a chloride, bromide, phosphate, sulphate, nitrate, acetate, or carbonate of Zn, Fe, Al, Mg or Ca.ALSO:Therapeutic compositions comprise as the active ingredient a disubstituted pyrazine of the formula <FORM:1113262/A5-A6/1> where R1 is alkyl and R2 is alkyl, carboxyl, alkoxycarbonyl, carbamoyl or mono- or dialkyl substituted carbamoyl, said alkyl groups containing 1 to 4 carbon atoms, or a physiologically acceptable salt thereof, dispersed in a solid vehicle or in a liquid which is a non-solvent for the active ingredient. The compositions may be formulated as tablets, pills, capsules, powders, wafers, cachets, granules and oral or parenteral fluid preparations and may include other therapeutic agents i.e. tolbutamide, N-(hexahydro-1-azepinyl - carbamoyl-p-toluene sulphonamide, chlorpropamide, phenformin hydrochloride, 5-methylpyrazole-3-carboxylic acid, inesoxalic acid, insulin, incotinic acid, the D-isomer of 3, 5, 31-triiodothyronine, triiodothyropropionic acid sodium-L-thyroxine, sodium D-thyroxine, hydrocortisone, prednisolone, 6a -methyl-prednisolone, anticoagulants, unsaturated fatty acids, vitamins, estrogens, androgens, antibiotics, analgesics, compounds associated with cholesterol synthesis or metabolism, lipotropic agents, amino acids, sterols, diuretics, anorexigenic agents and cardiovascular agents.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38979164A | 1964-08-14 | 1964-08-14 | |
| US44443265A | 1965-03-31 | 1965-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1113262A true GB1113262A (en) | 1968-05-08 |
Family
ID=27012842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25938/65A Expired GB1113262A (en) | 1964-08-14 | 1965-06-18 | Improvements in or relating to substituted pyrazines and the manufacture thereof |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3452014A (en) |
| BE (1) | BE668306A (en) |
| FR (1) | FR4615M (en) |
| GB (1) | GB1113262A (en) |
| IL (1) | IL23887A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1361967A (en) * | 1972-04-28 | 1974-07-30 | Erba Carlo Spa | Pyrazine 4-oxide derivatives and process for their preparation |
| JPS609726B2 (en) * | 1980-05-15 | 1985-03-12 | 株式会社 ミドリ十字 | steroid preparations |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB597889A (en) * | 1943-12-10 | 1948-02-05 | Merck & Co Inc | The manufacture of 2-amino-5-methyl pyrazine |
| US3067199A (en) * | 1956-09-13 | 1962-12-04 | Wyandotte Chemicals Corp | Method for preparing alkyl-substituted piperazines, alkyl-substituted pyrazines, andmixtures thereof |
-
1965
- 1965-03-31 US US444432A patent/US3452014A/en not_active Expired - Lifetime
- 1965-06-18 GB GB25938/65A patent/GB1113262A/en not_active Expired
- 1965-07-05 IL IL23887A patent/IL23887A/en unknown
- 1965-08-13 FR FR28295A patent/FR4615M/fr not_active Expired
- 1965-08-13 BE BE668306A patent/BE668306A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR4615M (en) | 1966-11-21 |
| BE668306A (en) | 1966-02-14 |
| US3452014A (en) | 1969-06-24 |
| IL23887A (en) | 1969-05-28 |
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