FI61880C - Foerfarande foer framstaellning av n-arylsulfonyl-n'-(3-azabicykloalkyl)-urinaemnen - Google Patents
Foerfarande foer framstaellning av n-arylsulfonyl-n'-(3-azabicykloalkyl)-urinaemnen Download PDFInfo
- Publication number
- FI61880C FI61880C FI2036/74A FI203674A FI61880C FI 61880 C FI61880 C FI 61880C FI 2036/74 A FI2036/74 A FI 2036/74A FI 203674 A FI203674 A FI 203674A FI 61880 C FI61880 C FI 61880C
- Authority
- FI
- Finland
- Prior art keywords
- urea
- azabicyclo
- general formula
- dimethylformamide
- compound
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 235000013877 carbamide Nutrition 0.000 claims description 10
- 229960000583 acetic acid Drugs 0.000 claims description 9
- 238000007792 addition Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000012362 glacial acetic acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 150000003672 ureas Chemical class 0.000 claims description 7
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- MRSMDCOLJUEYKQ-UHFFFAOYSA-N 1-(3-azabicyclo[3.1.0]hexan-3-yl)-3-(4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CC2C1 MRSMDCOLJUEYKQ-UHFFFAOYSA-N 0.000 claims 1
- LFKZTPFEZNFDOE-UHFFFAOYSA-N 1-(3-azabicyclo[3.2.0]heptan-3-yl)-3-(4-chlorophenyl)sulfonylurea Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCC2C1 LFKZTPFEZNFDOE-UHFFFAOYSA-N 0.000 claims 1
- WNHZTXOJJUDJHP-UHFFFAOYSA-N 1-(3-azabicyclo[3.2.0]heptan-3-yl)-3-(4-ethylphenyl)sulfonylurea Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCC2C1 WNHZTXOJJUDJHP-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- FSCBDDOKZIRLCN-UHFFFAOYSA-N 2-nitroso-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole Chemical compound C1CCC2CN(N=O)CC21 FSCBDDOKZIRLCN-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- BOVGTQGAOIONJV-UHFFFAOYSA-N gliclazide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CC2CCCC2C1 BOVGTQGAOIONJV-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RLEPMHBHXGEBBX-UHFFFAOYSA-N 2,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C1CCC2C(=O)NCC21 RLEPMHBHXGEBBX-UHFFFAOYSA-N 0.000 description 4
- QCWDCTDYSDJKTP-UHFFFAOYSA-N 4,5,6,6a-tetrahydro-3ah-cyclopenta[c]pyrrole-1,3-dione Chemical compound C1CCC2C(=O)NC(=O)C21 QCWDCTDYSDJKTP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FJYWNYLUZBMVKI-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-amine Chemical compound C1CCC2CN(N)CC21 FJYWNYLUZBMVKI-UHFFFAOYSA-N 0.000 description 3
- WPYNXKFLSQEEFE-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-amine;hydrochloride Chemical compound Cl.C1CCC2CN(N)CC21 WPYNXKFLSQEEFE-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- AEJRNONYXDAILM-UHFFFAOYSA-N [Ba+2].[O-][Cr]([O-])=O Chemical compound [Ba+2].[O-][Cr]([O-])=O AEJRNONYXDAILM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- OKQXTJACOYBNJC-UHFFFAOYSA-N ethyl 2-cyanocyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=C(C#N)CCC1 OKQXTJACOYBNJC-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HVZRRRPCVOJOLJ-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole;hydrochloride Chemical compound Cl.C1NCC2CCCC21 HVZRRRPCVOJOLJ-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- FMRNHWPEOPGATH-UHFFFAOYSA-N 1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-bromophenyl)sulfonylurea Chemical compound BrC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCCC2C1 FMRNHWPEOPGATH-UHFFFAOYSA-N 0.000 description 1
- WRMOWNXORINHPP-UHFFFAOYSA-N 1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-chlorophenyl)sulfonylurea Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCCC2C1 WRMOWNXORINHPP-UHFFFAOYSA-N 0.000 description 1
- IBJVOFLXIKQLIS-UHFFFAOYSA-N 1-(3-azabicyclo[3.2.0]heptan-3-yl)-3-(4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCC2C1 IBJVOFLXIKQLIS-UHFFFAOYSA-N 0.000 description 1
- FVEAFBOATJVRDS-UHFFFAOYSA-N 2-cyanocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1C#N FVEAFBOATJVRDS-UHFFFAOYSA-N 0.000 description 1
- RIEDWFNWOPCCPM-UHFFFAOYSA-N CCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2 Chemical compound CCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2 RIEDWFNWOPCCPM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 101000956900 Mesobuthus martensii HMG-CoA reductase inhibitor bumarsin Proteins 0.000 description 1
- SCZFLGPSHHAROT-UHFFFAOYSA-N [Cr].[Ba] Chemical compound [Cr].[Ba] SCZFLGPSHHAROT-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000009101 diabetic angiopathy Diseases 0.000 description 1
- 201000002249 diabetic peripheral angiopathy Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- TXAQXDWPENKEDF-UHFFFAOYSA-N ethyl 2-cyanocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1C#N TXAQXDWPENKEDF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA175626 | 1973-07-04 | ||
| CA175626 | 1973-07-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI203674A7 FI203674A7 (cs) | 1975-01-05 |
| FI61880B FI61880B (fi) | 1982-06-30 |
| FI61880C true FI61880C (fi) | 1982-10-11 |
Family
ID=4097201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2036/74A FI61880C (fi) | 1973-07-04 | 1974-07-03 | Foerfarande foer framstaellning av n-arylsulfonyl-n'-(3-azabicykloalkyl)-urinaemnen |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5333584B2 (cs) |
| AR (1) | AR203750A1 (cs) |
| AT (1) | AT339914B (cs) |
| CS (1) | CS185566B2 (cs) |
| DD (1) | DD113223A5 (cs) |
| DK (1) | DK137752B (cs) |
| ES (1) | ES427972A1 (cs) |
| FI (1) | FI61880C (cs) |
| HU (1) | HU168450B (cs) |
| IN (1) | IN139716B (cs) |
| NO (1) | NO144344C (cs) |
| OA (1) | OA04735A (cs) |
| PH (1) | PH12355A (cs) |
| RO (1) | RO70080A (cs) |
| SE (1) | SE399424B (cs) |
| SU (1) | SU552896A3 (cs) |
| YU (1) | YU40105B (cs) |
| ZA (1) | ZA744313B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183857A (en) * | 1978-07-06 | 1980-01-15 | Shell Oil Company | 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione |
| CA1121355A (en) * | 1978-10-27 | 1982-04-06 | Ronald F. Mason | Pyrrolidine derivatives and process for the preparation of such compounds |
| FR2610321B1 (fr) * | 1987-02-04 | 1989-04-07 | Oril Sa | Nouveau procede de synthese du n-amino aza-3 bicyclo (3, 3, 0) octane |
| CN105061293B (zh) * | 2015-07-28 | 2017-11-07 | 江苏瑞科医药科技有限公司 | 一种格列齐特中间体氨基氮杂环盐酸盐的合成方法 |
| CN110372545B (zh) * | 2019-08-06 | 2022-01-04 | 山东海佑福瑞达制药有限公司 | 一种高纯度的格列齐特中间体对甲苯磺酰脲的制备方法 |
| CN110372568A (zh) * | 2019-08-22 | 2019-10-25 | 山东海佑福瑞达制药有限公司 | 一种格列齐特中间体的结晶及其制备方法 |
| RU2754708C1 (ru) * | 2021-03-02 | 2021-09-06 | Акционерное общество "Щелково Агрохим" | Способ получения гликлазида |
-
1974
- 1974-06-05 YU YU1566/74A patent/YU40105B/xx unknown
- 1974-06-11 IN IN1269/CAL/74A patent/IN139716B/en unknown
- 1974-06-27 AR AR254427A patent/AR203750A1/es active
- 1974-06-27 OA OA55236A patent/OA04735A/xx unknown
- 1974-07-01 CS CS7400004621A patent/CS185566B2/cs unknown
- 1974-07-02 RO RO7479387A patent/RO70080A/ro unknown
- 1974-07-02 DK DK354474AA patent/DK137752B/da not_active IP Right Cessation
- 1974-07-02 DD DD179654A patent/DD113223A5/xx unknown
- 1974-07-03 HU HUSI1420A patent/HU168450B/hu not_active IP Right Cessation
- 1974-07-03 SE SE7408755A patent/SE399424B/xx not_active IP Right Cessation
- 1974-07-03 JP JP7624474A patent/JPS5333584B2/ja not_active Expired
- 1974-07-03 NO NO742425A patent/NO144344C/no unknown
- 1974-07-03 FI FI2036/74A patent/FI61880C/fi active
- 1974-07-03 PH PH7416011A patent/PH12355A/en unknown
- 1974-07-03 SU SU2041822A patent/SU552896A3/ru active
- 1974-07-04 ES ES427972A patent/ES427972A1/es not_active Expired
- 1974-07-04 ZA ZA00744313A patent/ZA744313B/xx unknown
- 1974-07-04 AT AT553074A patent/AT339914B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5062971A (cs) | 1975-05-29 |
| FI203674A7 (cs) | 1975-01-05 |
| DK354474A (cs) | 1975-02-24 |
| FI61880B (fi) | 1982-06-30 |
| ES427972A1 (es) | 1976-08-16 |
| HU168450B (cs) | 1976-04-28 |
| NO742425L (cs) | 1975-02-03 |
| OA04735A (fr) | 1980-08-31 |
| DK137752B (da) | 1978-05-01 |
| DK137752C (cs) | 1978-10-02 |
| ZA744313B (en) | 1975-07-30 |
| YU40105B (en) | 1985-08-31 |
| IN139716B (cs) | 1976-07-24 |
| YU156674A (en) | 1983-01-21 |
| SE7408755L (cs) | 1975-01-07 |
| AT339914B (de) | 1977-11-10 |
| SE399424B (sv) | 1978-02-13 |
| AR203750A1 (es) | 1975-10-15 |
| ATA553074A (de) | 1977-03-15 |
| RO70080A (ro) | 1980-06-15 |
| NO144344C (no) | 1981-08-12 |
| DD113223A5 (cs) | 1975-05-20 |
| NO144344B (no) | 1981-05-04 |
| SU552896A3 (ru) | 1977-03-30 |
| CS185566B2 (en) | 1978-10-31 |
| PH12355A (en) | 1979-01-29 |
| JPS5333584B2 (cs) | 1978-09-14 |
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