DE1946751A1 - 3-Acyl-gamma-resorcylsaeure-anilide und Verfahren zu ihrer Herstellung - Google Patents
3-Acyl-gamma-resorcylsaeure-anilide und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1946751A1 DE1946751A1 DE19691946751 DE1946751A DE1946751A1 DE 1946751 A1 DE1946751 A1 DE 1946751A1 DE 19691946751 DE19691946751 DE 19691946751 DE 1946751 A DE1946751 A DE 1946751A DE 1946751 A1 DE1946751 A1 DE 1946751A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- hydrogen
- trifluoromethyl
- anilide
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 S-acid anilides Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000003931 anilides Chemical class 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical group N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 4
- 241000242711 Fasciola hepatica Species 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 208000006275 fascioliasis Diseases 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UIPIHJQNWPTPIO-UHFFFAOYSA-N 2,6-diacetyloxybenzoic acid Chemical compound CC(=O)OC1=CC=CC(OC(C)=O)=C1C(O)=O UIPIHJQNWPTPIO-UHFFFAOYSA-N 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 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
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60M—POWER SUPPLY LINES, AND DEVICES ALONG RAILS, FOR ELECTRICALLY- PROPELLED VEHICLES
- B60M1/00—Power supply lines for contact with collector on vehicle
- B60M1/30—Power rails
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE756232D BE756232A (fr) | 1969-09-16 | Anilides de l'acide 3-acyl-alpha-resorcylique et leur preparation | |
| DE19691946751 DE1946751A1 (de) | 1969-09-16 | 1969-09-16 | 3-Acyl-gamma-resorcylsaeure-anilide und Verfahren zu ihrer Herstellung |
| BR215195/69A BR6915195D0 (pt) | 1969-09-16 | 1969-12-16 | Processo para a preparacao de anilidas de acidos 3-acilgama-resorcilicos |
| IE1092/70A IE34481B1 (en) | 1969-09-16 | 1970-08-20 | 3-acyl-ypsilon-resorcylic acid anilides and process for their manufacture |
| IL35146A IL35146A0 (en) | 1969-09-16 | 1970-08-21 | 3-acyl-gamma-resorcylic acid anilides and process for their manufacture |
| ZA705832A ZA705832B (en) | 1969-09-16 | 1970-08-25 | 3-acyl- -resorcylic acid anilides and process for their manufacture |
| US68775A US3681458A (en) | 1969-09-16 | 1970-09-01 | 3-acyl-{65 -resorcylic acid anilides |
| NL7013243A NL7013243A (en, 2012) | 1969-09-16 | 1970-09-08 | |
| BG015643A BG16738A3 (bg) | 1969-09-16 | 1970-09-12 | Метод за получаване на анимиди на 3-ацил-р-резорциновата киселина |
| AU19869/70A AU1986970A (en) | 1969-09-16 | 1970-09-14 | 3-acyl-8-resorcylic anilides and process for their manufacture |
| CH1362070A CH537906A (de) | 1969-09-16 | 1970-09-14 | Verfahren zur Herstellung von 3-Acyl-y-resorcylsäureaniliden |
| IT29764/70A IT1043950B (it) | 1969-09-16 | 1970-09-15 | Anilidi di acidi 3 acil gamma resorcilici e processo per la loro preparazione |
| ES383653A ES383653A1 (es) | 1969-09-16 | 1970-09-15 | Procedimiento de preparacion de anilidas de acido 3-acil- gamma-resorcilico. |
| FR7033563A FR2070076B1 (en, 2012) | 1969-09-16 | 1970-09-16 | |
| GB44224/70A GB1284682A (en) | 1969-09-16 | 1970-09-16 | 3-ACYL gamma-RESORCYLIC ACID ANILIDES AND PROCESSES FOR THEIR MANUFACTURE |
| AT838370A AT302279B (de) | 1969-09-16 | 1970-09-16 | Verfahren zur Herstellung von neuen 3-Acyl-γ-resorcylsäure-aniliden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691946751 DE1946751A1 (de) | 1969-09-16 | 1969-09-16 | 3-Acyl-gamma-resorcylsaeure-anilide und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1946751A1 true DE1946751A1 (de) | 1971-04-01 |
Family
ID=5745588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691946751 Pending DE1946751A1 (de) | 1969-09-16 | 1969-09-16 | 3-Acyl-gamma-resorcylsaeure-anilide und Verfahren zu ihrer Herstellung |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3681458A (en, 2012) |
| AT (1) | AT302279B (en, 2012) |
| AU (1) | AU1986970A (en, 2012) |
| BE (1) | BE756232A (en, 2012) |
| BG (1) | BG16738A3 (en, 2012) |
| BR (1) | BR6915195D0 (en, 2012) |
| CH (1) | CH537906A (en, 2012) |
| DE (1) | DE1946751A1 (en, 2012) |
| ES (1) | ES383653A1 (en, 2012) |
| FR (1) | FR2070076B1 (en, 2012) |
| GB (1) | GB1284682A (en, 2012) |
| IE (1) | IE34481B1 (en, 2012) |
| IL (1) | IL35146A0 (en, 2012) |
| IT (1) | IT1043950B (en, 2012) |
| NL (1) | NL7013243A (en, 2012) |
| ZA (1) | ZA705832B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287191A (en) * | 1980-04-14 | 1981-09-01 | The Research Foundation Of State University Of New York | Novel salicylanilides and microbiocidal compositions and uses thereof |
| US4358443A (en) * | 1980-04-14 | 1982-11-09 | The Research Foundation Of State University Of New York | Method and composition for controlling the growth of microorganisms |
| US4939132A (en) * | 1985-04-15 | 1990-07-03 | The Research Foundation Of State University Of New York | Novel 5-alkylsulfonylsalicylanilides and microbiocidal compositions for controlling the growth of microorganisms |
| WO2002049632A1 (fr) * | 2000-12-18 | 2002-06-27 | Institute Of Medicinal Molecular Design. Inc. | Inhibiteurs de production et de liberation de cytokines inflammatoires |
| AU2003242098B2 (en) * | 2002-06-10 | 2008-11-20 | Institute Of Medicinal Molecular Design, Inc | Inhibitors against activation of NFkappaB |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449420A (en) * | 1966-01-15 | 1969-06-10 | Hoechst Ag | Gamma-resorcylic acid anilides and process for preparing them |
| DE1668080A1 (de) * | 1968-01-18 | 1971-07-22 | Hoechst Ag | Verfahren zur Herstellung von 3-Nitro-gamma-resorcylsaeureaniliden |
-
0
- BE BE756232D patent/BE756232A/xx unknown
-
1969
- 1969-09-16 DE DE19691946751 patent/DE1946751A1/de active Pending
- 1969-12-16 BR BR215195/69A patent/BR6915195D0/pt unknown
-
1970
- 1970-08-20 IE IE1092/70A patent/IE34481B1/xx unknown
- 1970-08-21 IL IL35146A patent/IL35146A0/xx unknown
- 1970-08-25 ZA ZA705832A patent/ZA705832B/xx unknown
- 1970-09-01 US US68775A patent/US3681458A/en not_active Expired - Lifetime
- 1970-09-08 NL NL7013243A patent/NL7013243A/xx unknown
- 1970-09-12 BG BG015643A patent/BG16738A3/xx unknown
- 1970-09-14 AU AU19869/70A patent/AU1986970A/en not_active Expired
- 1970-09-14 CH CH1362070A patent/CH537906A/de not_active IP Right Cessation
- 1970-09-15 IT IT29764/70A patent/IT1043950B/it active
- 1970-09-15 ES ES383653A patent/ES383653A1/es not_active Expired
- 1970-09-16 FR FR7033563A patent/FR2070076B1/fr not_active Expired
- 1970-09-16 GB GB44224/70A patent/GB1284682A/en not_active Expired
- 1970-09-16 AT AT838370A patent/AT302279B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| IL35146A0 (en) | 1970-10-30 |
| GB1284682A (en) | 1972-08-09 |
| BE756232A (fr) | 1971-03-16 |
| IE34481L (en) | 1971-03-16 |
| BG16738A3 (bg) | 1973-02-15 |
| FR2070076A1 (en, 2012) | 1971-09-10 |
| BR6915195D0 (pt) | 1973-02-13 |
| AU1986970A (en) | 1972-03-16 |
| FR2070076B1 (en, 2012) | 1973-12-21 |
| AT302279B (de) | 1972-10-10 |
| NL7013243A (en, 2012) | 1971-03-18 |
| US3681458A (en) | 1972-08-01 |
| IE34481B1 (en) | 1975-05-28 |
| ES383653A1 (es) | 1973-07-01 |
| ZA705832B (en) | 1971-04-28 |
| CH537906A (de) | 1973-06-15 |
| IT1043950B (it) | 1980-02-29 |
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