DK142649B - Analogifremgangsmåde til fremstilling af substituerede tetrazoler. - Google Patents
Analogifremgangsmåde til fremstilling af substituerede tetrazoler. Download PDFInfo
- Publication number
- DK142649B DK142649B DK168678A DK168678A DK142649B DK 142649 B DK142649 B DK 142649B DK 168678 A DK168678 A DK 168678A DK 168678 A DK168678 A DK 168678A DK 142649 B DK142649 B DK 142649B
- Authority
- DK
- Denmark
- Prior art keywords
- quinoline
- ylcarbamoyl
- tetrazol
- compounds
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- 150000003536 tetrazoles Chemical class 0.000 title description 8
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- -1 8-substituted quinolines Chemical class 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical class C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012048 reactive intermediate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XDWZRFWGJDEHOX-UHFFFAOYSA-N 1-[chloro(phenoxy)methyl]-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(Cl)OC1=CC=CC=C1 XDWZRFWGJDEHOX-UHFFFAOYSA-N 0.000 description 1
- GTKOKCQMHAGFSM-UHFFFAOYSA-N 1-methyltetrazol-5-amine Chemical compound CN1N=NN=C1N GTKOKCQMHAGFSM-UHFFFAOYSA-N 0.000 description 1
- BMSUMBVAEYUOBI-UHFFFAOYSA-N 2,4-dimethyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C12=NC(C)=CC(C)=C2C=CC=C1C(=O)NC1=NN=NN1 BMSUMBVAEYUOBI-UHFFFAOYSA-N 0.000 description 1
- LPFHSFQYEOWNJJ-UHFFFAOYSA-N 2,4-dimethylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC(C)=C21 LPFHSFQYEOWNJJ-UHFFFAOYSA-N 0.000 description 1
- OIUQZVNRCPPCKW-UHFFFAOYSA-N 2-methyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C12=NC(C)=CC=C2C=CC=C1C(=O)NC1=NN=NN1 OIUQZVNRCPPCKW-UHFFFAOYSA-N 0.000 description 1
- AZUKLCJYWVMPML-UHFFFAOYSA-N 2-methyltetrazol-5-amine Chemical compound CN1N=NC(N)=N1 AZUKLCJYWVMPML-UHFFFAOYSA-N 0.000 description 1
- JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 1
- MYIKCCSCXPRLQB-UHFFFAOYSA-N 4-methyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C1=CC=C2C(C)=CC=NC2=C1C(=O)NC=1N=NNN=1 MYIKCCSCXPRLQB-UHFFFAOYSA-N 0.000 description 1
- VENLCDVXWFXNOE-UHFFFAOYSA-N 5-chloro-4-methyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C1=CC(Cl)=C2C(C)=CC=NC2=C1C(=O)NC1=NN=NN1 VENLCDVXWFXNOE-UHFFFAOYSA-N 0.000 description 1
- JAZWJAUVCXLIMF-UHFFFAOYSA-N 5-chloro-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C12=NC=CC=C2C(Cl)=CC=C1C(=O)NC=1N=NNN=1 JAZWJAUVCXLIMF-UHFFFAOYSA-N 0.000 description 1
- RWIZYGAQRJHZSB-UHFFFAOYSA-N 5-methoxy-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C12=NC=CC=C2C(OC)=CC=C1C(=O)NC1=NN=NN1 RWIZYGAQRJHZSB-UHFFFAOYSA-N 0.000 description 1
- HJUQVGOXHAHWKV-UHFFFAOYSA-N 5-methyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C12=NC=CC=C2C(C)=CC=C1C(=O)NC=1N=NNN=1 HJUQVGOXHAHWKV-UHFFFAOYSA-N 0.000 description 1
- MUBIMTBRVDYVKF-UHFFFAOYSA-N 6-chloro-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C=12N=CC=CC2=CC(Cl)=CC=1C(=O)NC1=NN=NN1 MUBIMTBRVDYVKF-UHFFFAOYSA-N 0.000 description 1
- WFYMBUYPCJNOGE-UHFFFAOYSA-N 6-hydroxy-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C=12N=CC=CC2=CC(O)=CC=1C(=O)NC1=NN=NN1 WFYMBUYPCJNOGE-UHFFFAOYSA-N 0.000 description 1
- KHUOBAVAPCBDKX-UHFFFAOYSA-N 6-iodo-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C=12N=CC=CC2=CC(I)=CC=1C(=O)NC1=NN=NN1 KHUOBAVAPCBDKX-UHFFFAOYSA-N 0.000 description 1
- JSSZKBQHCNZYCC-UHFFFAOYSA-N 6-methyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C=12N=CC=CC2=CC(C)=CC=1C(=O)NC1=NN=NN1 JSSZKBQHCNZYCC-UHFFFAOYSA-N 0.000 description 1
- CULNSKHQWJAINH-UHFFFAOYSA-N 6-nitro-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound C=12N=CC=CC2=CC([N+](=O)[O-])=CC=1C(=O)NC=1N=NNN=1 CULNSKHQWJAINH-UHFFFAOYSA-N 0.000 description 1
- DFZDNTXKIUEFGH-UHFFFAOYSA-N 7-methyl-n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical compound CC1=CC=C2C=CC=NC2=C1C(=O)NC1=NN=NN1 DFZDNTXKIUEFGH-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 208000004262 Food Hypersensitivity Diseases 0.000 description 1
- 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 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 208000002205 allergic conjunctivitis Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000024998 atopic conjunctivitis Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- XQKRYBXCYCKQLL-UHFFFAOYSA-N dimethylaminomethanol Chemical compound CN(C)CO XQKRYBXCYCKQLL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 208000024711 extrinsic asthma Diseases 0.000 description 1
- 235000020932 food allergy Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MTIPWRREDRHLTI-UHFFFAOYSA-N n-(1-methyltetrazol-5-yl)quinoline-8-carboxamide Chemical compound CN1N=NN=C1NC(=O)C1=CC=CC2=CC=CN=C12 MTIPWRREDRHLTI-UHFFFAOYSA-N 0.000 description 1
- NHLVACWSZDGZNV-UHFFFAOYSA-N n-(2-methyl-1,3-dihydrotetrazol-5-yl)quinoline-8-carboxamide Chemical compound N1N(C)NN=C1NC(=O)C1=CC=CC2=CC=CN=C12 NHLVACWSZDGZNV-UHFFFAOYSA-N 0.000 description 1
- VSMCHFPJPJNCEE-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)quinoline-8-carboxamide Chemical group C=1C=CC2=CC=CN=C2C=1C(=O)NC1=NN=NN1 VSMCHFPJPJNCEE-UHFFFAOYSA-N 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GBNJBBLCLJCAPR-UHFFFAOYSA-N tetrazol-2-amine;hydrate Chemical compound O.NN1N=CN=N1 GBNJBBLCLJCAPR-UHFFFAOYSA-N 0.000 description 1
- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical group [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK168678A DK142649B (da) | 1978-04-18 | 1978-04-18 | Analogifremgangsmåde til fremstilling af substituerede tetrazoler. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK168678 | 1978-04-18 | ||
| DK168678A DK142649B (da) | 1978-04-18 | 1978-04-18 | Analogifremgangsmåde til fremstilling af substituerede tetrazoler. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK168678A DK168678A (en, 2012) | 1979-10-19 |
| DK142649B true DK142649B (da) | 1980-12-08 |
| DK142649C DK142649C (en, 2012) | 1981-08-10 |
Family
ID=8107199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK168678A DK142649B (da) | 1978-04-18 | 1978-04-18 | Analogifremgangsmåde til fremstilling af substituerede tetrazoler. |
Country Status (1)
| Country | Link |
|---|---|
| DK (1) | DK142649B (en, 2012) |
-
1978
- 1978-04-18 DK DK168678A patent/DK142649B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK168678A (en, 2012) | 1979-10-19 |
| DK142649C (en, 2012) | 1981-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed | ||
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |