DE2403060C3 - 3-Carbamoyl-1-thia-isochroman-1,1-dioxide und Verfahn zu ihrer Herstellung - Google Patents
3-Carbamoyl-1-thia-isochroman-1,1-dioxide und Verfahn zu ihrer HerstellungInfo
- Publication number
- DE2403060C3 DE2403060C3 DE2403060A DE2403060A DE2403060C3 DE 2403060 C3 DE2403060 C3 DE 2403060C3 DE 2403060 A DE2403060 A DE 2403060A DE 2403060 A DE2403060 A DE 2403060A DE 2403060 C3 DE2403060 C3 DE 2403060C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- general formula
- compounds
- dioxide
- thia
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims 2
- DMHRVJJBVONOCS-UHFFFAOYSA-N 1,1-dioxo-3,4-dihydro-2,1lambda6-benzoxathiine-3-carboxamide Chemical compound C(N)(=O)C1OS(C2=CC=CC=C2C1)(=O)=O DMHRVJJBVONOCS-UHFFFAOYSA-N 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- -1 aliphatic ketones Chemical class 0.000 claims description 8
- 229940093915 gynecological organic acid Drugs 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 229940074355 nitric acid Drugs 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 claims description 2
- 229940087675 benzilic acid Drugs 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 229960004365 benzoic acid Drugs 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229940013688 formic acid Drugs 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 235000011087 fumaric acid Nutrition 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229940116315 oxalic acid Drugs 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004838 phosphoric acid Drugs 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 229940095574 propionic acid Drugs 0.000 claims description 2
- 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 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 229940032330 sulfuric acid Drugs 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 229960004592 isopropanol Drugs 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- SAKGOYVQTSICKT-UHFFFAOYSA-N 2-n,2-dimethylpentane-2,4-diamine Chemical compound CNC(C)(C)CC(C)N SAKGOYVQTSICKT-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- FAZVYQPQIRUWRJ-UHFFFAOYSA-N 6,7-dimethoxy-1,1-dioxo-3,4-dihydro-2,1lambda6-benzoxathiine-3-carbonyl chloride Chemical compound COC1=C(OC)C=C2C(CC(OS2(=O)=O)C(Cl)=O)=C1 FAZVYQPQIRUWRJ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 210000002196 fr. b Anatomy 0.000 description 2
- 210000003918 fraction a Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- YXBPGEDCLHNGHJ-UHFFFAOYSA-N 2-N-benzyl-2-methylpentane-2,4-diamine Chemical compound C(C1=CC=CC=C1)NC(C)(CC(C)N)C YXBPGEDCLHNGHJ-UHFFFAOYSA-N 0.000 description 1
- RIHGEIMDTCIVNX-UHFFFAOYSA-N 2-N-butan-2-yl-2-methylpentane-2,4-diamine Chemical compound CCC(C)NC(C)(C)CC(C)N RIHGEIMDTCIVNX-UHFFFAOYSA-N 0.000 description 1
- TXTDUELHKFMSAN-UHFFFAOYSA-N 2-N-hexyl-2-methylpentane-2,4-diamine Chemical compound C(CCCCC)NC(C)(CC(C)N)C TXTDUELHKFMSAN-UHFFFAOYSA-N 0.000 description 1
- ZSXVXTYIYICOIO-UHFFFAOYSA-N 2-methyl-2-N-propylpentane-2,4-diamine Chemical compound C(CC)NC(C)(CC(C)N)C ZSXVXTYIYICOIO-UHFFFAOYSA-N 0.000 description 1
- JAOZSXMVXGUJFX-UHFFFAOYSA-N 2-methyl-2-n-(2-methylpropyl)pentane-2,4-diamine Chemical compound CC(C)CNC(C)(C)CC(C)N JAOZSXMVXGUJFX-UHFFFAOYSA-N 0.000 description 1
- FAXMAGSAFLZSNW-UHFFFAOYSA-N 2-methyl-2-n-propan-2-ylpentane-2,4-diamine Chemical compound CC(C)NC(C)(C)CC(C)N FAXMAGSAFLZSNW-UHFFFAOYSA-N 0.000 description 1
- GNBARLLWIAIBIR-UHFFFAOYSA-N 2-n-butyl-2-methylpentane-2,4-diamine Chemical compound CCCCNC(C)(C)CC(C)N GNBARLLWIAIBIR-UHFFFAOYSA-N 0.000 description 1
- ZKRSEUBKYMIMQG-UHFFFAOYSA-N 2-n-cyclohexyl-2-methylpentane-2,4-diamine Chemical compound CC(N)CC(C)(C)NC1CCCCC1 ZKRSEUBKYMIMQG-UHFFFAOYSA-N 0.000 description 1
- CHQRREGJXJBETL-UHFFFAOYSA-N COC1OS(C2=CC=CC=C2C1)(=O)=O Chemical compound COC1OS(C2=CC=CC=C2C1)(=O)=O CHQRREGJXJBETL-UHFFFAOYSA-N 0.000 description 1
- OTVSNYKQOCLWKI-UHFFFAOYSA-N Cl.CNC(C)(CC(C)N)C Chemical compound Cl.CNC(C)(CC(C)N)C OTVSNYKQOCLWKI-UHFFFAOYSA-N 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- OWKYZAGJTTTXOK-UHFFFAOYSA-N n'-propylpropane-1,3-diamine Chemical compound CCCNCCCN OWKYZAGJTTTXOK-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD170664A DD109389A1 (ro) | 1973-05-02 | 1973-05-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2403060A1 DE2403060A1 (de) | 1974-11-21 |
| DE2403060B2 DE2403060B2 (de) | 1980-07-03 |
| DE2403060C3 true DE2403060C3 (de) | 1981-04-02 |
Family
ID=5491127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2403060A Expired DE2403060C3 (de) | 1973-05-02 | 1974-01-23 | 3-Carbamoyl-1-thia-isochroman-1,1-dioxide und Verfahn zu ihrer Herstellung |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5519221B2 (ro) |
| AT (1) | AT330196B (ro) |
| BE (1) | BE814031A (ro) |
| CH (1) | CH592650A5 (ro) |
| CS (1) | CS171495B1 (ro) |
| DD (1) | DD109389A1 (ro) |
| DE (1) | DE2403060C3 (ro) |
| DK (1) | DK133948B (ro) |
| FI (1) | FI56532C (ro) |
| FR (1) | FR2227871B1 (ro) |
| GB (1) | GB1407193A (ro) |
| HU (1) | HU167082B (ro) |
| NL (1) | NL7402317A (ro) |
| PL (1) | PL90399B1 (ro) |
| RO (2) | RO66098A (ro) |
| SE (1) | SE406469B (ro) |
| SU (1) | SU559923A1 (ro) |
-
1973
- 1973-05-02 DD DD170664A patent/DD109389A1/xx unknown
-
1974
- 1974-01-22 AT AT51674*#A patent/AT330196B/de not_active IP Right Cessation
- 1974-01-23 DE DE2403060A patent/DE2403060C3/de not_active Expired
- 1974-02-20 NL NL7402317A patent/NL7402317A/xx not_active Application Discontinuation
- 1974-03-14 JP JP2866274A patent/JPS5519221B2/ja not_active Expired
- 1974-03-22 CH CH406674A patent/CH592650A5/xx not_active IP Right Cessation
- 1974-04-19 GB GB1728874A patent/GB1407193A/en not_active Expired
- 1974-04-22 BE BE143478A patent/BE814031A/xx unknown
- 1974-04-29 FI FI1301/74A patent/FI56532C/fi active
- 1974-04-30 SU SU2020216A patent/SU559923A1/ru active
- 1974-04-30 PL PL1974170731A patent/PL90399B1/pl unknown
- 1974-04-30 SE SE747405825A patent/SE406469B/xx unknown
- 1974-05-01 RO RO7478636A patent/RO66098A/ro unknown
- 1974-05-01 RO RO7491543A patent/RO71551A/ro unknown
- 1974-05-01 DK DK237274AA patent/DK133948B/da unknown
- 1974-05-02 CS CS3135A patent/CS171495B1/cs unknown
- 1974-05-02 FR FR7415301A patent/FR2227871B1/fr not_active Expired
- 1974-05-02 HU HUAE415A patent/HU167082B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD109389A1 (ro) | 1974-11-05 |
| RO71551A (ro) | 1982-02-26 |
| RO66098A (ro) | 1981-07-30 |
| FI56532B (fi) | 1979-10-31 |
| CS171495B1 (ro) | 1976-10-29 |
| PL90399B1 (ro) | 1977-01-31 |
| HU167082B (ro) | 1975-08-28 |
| SU559923A1 (ru) | 1977-05-30 |
| GB1407193A (en) | 1975-09-24 |
| DK133948C (ro) | 1977-01-24 |
| AT330196B (de) | 1976-06-25 |
| FI56532C (fi) | 1980-02-11 |
| DE2403060B2 (de) | 1980-07-03 |
| JPS49135978A (ro) | 1974-12-27 |
| DE2403060A1 (de) | 1974-11-21 |
| DK133948B (da) | 1976-08-16 |
| NL7402317A (ro) | 1974-11-05 |
| SE406469B (sv) | 1979-02-12 |
| ATA51674A (de) | 1975-09-15 |
| JPS5519221B2 (ro) | 1980-05-24 |
| CH592650A5 (ro) | 1977-10-31 |
| FR2227871B1 (ro) | 1978-02-03 |
| BE814031A (fr) | 1974-10-22 |
| FR2227871A1 (ro) | 1974-11-29 |
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