DE2412582A1 - 11h,12h- eckige klammer auf 1 eckige klammer zu benzopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzopyran-11,12-dion- und 11h,12h- eckige klammer auf 1 eckige klammer zu benzothiopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzothiopyran-11,12-dion-verbindungen - Google Patents
11h,12h- eckige klammer auf 1 eckige klammer zu benzopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzopyran-11,12-dion- und 11h,12h- eckige klammer auf 1 eckige klammer zu benzothiopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzothiopyran-11,12-dion-verbindungenInfo
- Publication number
- DE2412582A1 DE2412582A1 DE2412582A DE2412582A DE2412582A1 DE 2412582 A1 DE2412582 A1 DE 2412582A1 DE 2412582 A DE2412582 A DE 2412582A DE 2412582 A DE2412582 A DE 2412582A DE 2412582 A1 DE2412582 A1 DE 2412582A1
- Authority
- DE
- Germany
- Prior art keywords
- square
- brackets
- bracket
- dione
- angle
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 20
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 12
- -1 methylenedioxy Chemical group 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FERWUCFAQLAGDE-UHFFFAOYSA-N 1,3-bis(2-hydroxyphenyl)propane-1,3-dione Chemical compound OC1=CC=CC=C1C(=O)CC(=O)C1=CC=CC=C1O FERWUCFAQLAGDE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SBPRDYIPEHBDCW-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-phenylpropane-1,3-dione Chemical compound COC1=CC=CC=C1C(=O)CC(=O)C1=CC=CC=C1 SBPRDYIPEHBDCW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- CNKOSVITQUOOGU-UHFFFAOYSA-N dimethyl 2-(dichloromethylidene)propanedioate Chemical compound COC(=O)C(=C(Cl)Cl)C(=O)OC CNKOSVITQUOOGU-UHFFFAOYSA-N 0.000 description 1
- WKMOUOHTNFTZSM-UHFFFAOYSA-N dimethyl 2-[bis(phenylsulfanyl)methylidene]propanedioate Chemical compound C=1C=CC=CC=1SC(=C(C(=O)OC)C(=O)OC)SC1=CC=CC=C1 WKMOUOHTNFTZSM-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2412582A DE2412582A1 (de) | 1974-03-15 | 1974-03-15 | 11h,12h- eckige klammer auf 1 eckige klammer zu benzopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzopyran-11,12-dion- und 11h,12h- eckige klammer auf 1 eckige klammer zu benzothiopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzothiopyran-11,12-dion-verbindungen |
| NL7502951A NL7502951A (nl) | 1974-03-15 | 1975-03-12 | Werkwijze ter bereiding van benzopyrano-benzo- pyranen en benzothiopyrano-benzothiopyranen, werkwijze ter bereiding van farmaceutische preparaten en gevormde preparaten. |
| US05/557,832 US3978081A (en) | 1974-03-15 | 1975-03-12 | 11H,12H-[1]benzopyrano[2,3-b][1]benzopyran-11,12-dione and derivatives |
| FR7507819A FR2263760B1 (https=) | 1974-03-15 | 1975-03-13 | |
| GB1078475A GB1463793A (en) | 1974-03-15 | 1975-03-14 | 11h-12h-1-benzopyrano-2,3-b- 1- benzopyran-11,12-dione compounds and 11h,12h-1-benzothiopyrano-2,3-b-1-benzothiopyran-11,12- dione compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2412582A DE2412582A1 (de) | 1974-03-15 | 1974-03-15 | 11h,12h- eckige klammer auf 1 eckige klammer zu benzopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzopyran-11,12-dion- und 11h,12h- eckige klammer auf 1 eckige klammer zu benzothiopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzothiopyran-11,12-dion-verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2412582A1 true DE2412582A1 (de) | 1975-10-02 |
Family
ID=5910211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2412582A Pending DE2412582A1 (de) | 1974-03-15 | 1974-03-15 | 11h,12h- eckige klammer auf 1 eckige klammer zu benzopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzopyran-11,12-dion- und 11h,12h- eckige klammer auf 1 eckige klammer zu benzothiopyrano eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1 eckige klammer zu benzothiopyran-11,12-dion-verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3978081A (https=) |
| DE (1) | DE2412582A1 (https=) |
| FR (1) | FR2263760B1 (https=) |
| GB (1) | GB1463793A (https=) |
| NL (1) | NL7502951A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4153719A (en) * | 1977-09-06 | 1979-05-08 | Sterling Drug Inc. | Aromatic diketones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752830A (en) * | 1971-02-04 | 1973-08-14 | Warner Lambert Co | Substituted pyrano(2,3-b)pyrans |
| US3842085A (en) * | 1972-02-04 | 1974-10-15 | Strandtmann M Von | Substituted pyrano(2,3-b)pyrans and process for their production |
-
1974
- 1974-03-15 DE DE2412582A patent/DE2412582A1/de active Pending
-
1975
- 1975-03-12 US US05/557,832 patent/US3978081A/en not_active Expired - Lifetime
- 1975-03-12 NL NL7502951A patent/NL7502951A/xx not_active Application Discontinuation
- 1975-03-13 FR FR7507819A patent/FR2263760B1/fr not_active Expired
- 1975-03-14 GB GB1078475A patent/GB1463793A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7502951A (nl) | 1975-09-17 |
| US3978081A (en) | 1976-08-31 |
| FR2263760B1 (https=) | 1978-10-27 |
| FR2263760A1 (https=) | 1975-10-10 |
| GB1463793A (en) | 1977-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |