DE2804293C2 - - Google Patents
Info
- Publication number
- DE2804293C2 DE2804293C2 DE19782804293 DE2804293A DE2804293C2 DE 2804293 C2 DE2804293 C2 DE 2804293C2 DE 19782804293 DE19782804293 DE 19782804293 DE 2804293 A DE2804293 A DE 2804293A DE 2804293 C2 DE2804293 C2 DE 2804293C2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- oxo
- methyl
- compounds
- butyrate
- 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
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- FDRDUFLWFSLNFT-UHFFFAOYSA-N 2-methyl-4-oxo-4-(4-phenylphenyl)butanoic acid Chemical compound C1=CC(C(=O)CC(C)C(O)=O)=CC=C1C1=CC=CC=C1 FDRDUFLWFSLNFT-UHFFFAOYSA-N 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- WOMMQCCRBNIOHF-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)phenyl]-2-methyl-4-oxobutanoic acid Chemical compound ClC1=C(C=CC=C1)C1=CC=C(C=C1)C(CC(C(=O)O)C)=O WOMMQCCRBNIOHF-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 claims description 3
- WMFHUUKYIUOHRA-UHFFFAOYSA-N (3-phenoxyphenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=CC(OC=2C=CC=CC=2)=C1 WMFHUUKYIUOHRA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 3
- 230000004968 inflammatory condition Effects 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000008014 pharmaceutical binder Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000011835 investigation Methods 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 208000008035 Back Pain Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 206010018691 Granuloma Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000008930 Low Back Pain Diseases 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 210000001541 thymus gland Anatomy 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- JWDYCNIAQWPBHD-UHFFFAOYSA-N 1-(2-methylphenyl)glycerol Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- 208000030090 Acute Disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 238000001838 alkalimetric titration Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229960003861 mephenesin Drugs 0.000 description 1
- 210000002346 musculoskeletal system Anatomy 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7702959A FR2378741A1 (fr) | 1977-02-01 | 1977-02-01 | Acides garyl goxo isovaleriques doues de proprietes antiphlogistiques et antalgiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2804293A1 DE2804293A1 (de) | 1978-08-10 |
| DE2804293C2 true DE2804293C2 (en, 2012) | 1989-08-03 |
Family
ID=9186227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782804293 Granted DE2804293A1 (de) | 1977-02-01 | 1978-02-01 | Alpha-aryl-gamma-oxo-isovaleriansaeure-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE863196A (en, 2012) |
| CA (1) | CA1097684A (en, 2012) |
| CH (1) | CH628014A5 (en, 2012) |
| DE (1) | DE2804293A1 (en, 2012) |
| ES (1) | ES466493A1 (en, 2012) |
| FR (1) | FR2378741A1 (en, 2012) |
| GB (1) | GB1565616A (en, 2012) |
| NL (1) | NL7801057A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS243570B1 (en) * | 1984-08-31 | 1986-06-12 | Miroslav Kuchar | Omega-aryloxoalkane acids |
| US5789434A (en) * | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| AR002945A1 (es) * | 1994-11-15 | 1998-05-27 | Bayer Corp | Acidos 4-biarilbutirico o 5-biarilpentanoico sustituidos y sus derivados como inhibidores de las metaloproteasas de matriz, composicion que los contiene, y metodos para la preparacion de dichos compuestos |
| US5886022A (en) * | 1995-06-05 | 1999-03-23 | Bayer Corporation | Substituted cycloalkanecarboxylic acid derivatives as matrix metalloprotease inhibitors |
| GB9522615D0 (en) * | 1995-11-03 | 1996-01-03 | Pharmacia Spa | 4-Phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
| US5863915A (en) * | 1996-05-15 | 1999-01-26 | Bayer Corporation | Substituted 4-arylbutyric acid derivatives as matrix metalloprotease |
| HRP970245B1 (en) | 1996-05-15 | 2002-06-30 | Bayer Ag | Biaryl acetilenes as matrix metalloprotease inhibitors |
| TNSN97086A1 (fr) * | 1996-05-15 | 2005-03-15 | Bayer Corp | La substitution des acides derivatives 4-albutyrique comme inhibiteurs de la matrice metalloprotease. |
-
1977
- 1977-02-01 FR FR7702959A patent/FR2378741A1/fr active Granted
-
1978
- 1978-01-23 BE BE184536A patent/BE863196A/xx not_active IP Right Cessation
- 1978-01-30 NL NL7801057A patent/NL7801057A/xx not_active Application Discontinuation
- 1978-01-30 CA CA295,903A patent/CA1097684A/fr not_active Expired
- 1978-01-31 ES ES466493A patent/ES466493A1/es not_active Expired
- 1978-02-01 CH CH110878A patent/CH628014A5/fr not_active IP Right Cessation
- 1978-02-01 GB GB404378A patent/GB1565616A/en not_active Expired
- 1978-02-01 DE DE19782804293 patent/DE2804293A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1565616A (en) | 1980-04-23 |
| FR2378741B1 (en, 2012) | 1980-02-22 |
| ES466493A1 (es) | 1979-05-01 |
| CA1097684A (fr) | 1981-03-17 |
| FR2378741A1 (fr) | 1978-08-25 |
| CH628014A5 (en) | 1982-02-15 |
| NL7801057A (nl) | 1978-08-03 |
| DE2804293A1 (de) | 1978-08-10 |
| BE863196A (fr) | 1978-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1518002B2 (de) | Isoflavane und Isoflavene und Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel | |
| DE2938041A1 (de) | Verfahren zur herstellung von retinoylhydroxysaeurederivaten und arzneimittel, das diese verbindungen enthaelt | |
| DE2751301A1 (de) | Glucofuranose-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2549783A1 (de) | Triglyceride mit entzuendungshemmender wirkung | |
| DE2804293C2 (en, 2012) | ||
| DE2462691C2 (en, 2012) | ||
| DE2040578C3 (de) | Analgetisch, antiinflammatorisch und antiulcerogen wirkendes Arzneimittel | |
| DE3821317A1 (de) | Thioharnstoffderivate | |
| EP0033075B1 (de) | Substituierte 1,8-Dihydroxy-9-(10H)anthracenone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2434929C2 (de) | p-Acetylaminophenolester von Phenylsalicylsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2318784A1 (de) | N-(2,4-dihydroxybenzoyl)-4-aminosalizylsaeure | |
| DE3005359C2 (de) | N-m-Trifluormethylphenylanthranilate von o-Alkoxycarbonylphenolen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0313935A2 (de) | Enolether von 6-Chlor-4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno(2,3-e)-1,2-thiazin-3-carbonsäureamid-1,1-dioxid, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| DE3046325C2 (de) | Pharmazeutische Mittel mit antiphlogistischer, antipyretischer und analgetischer Wirkung | |
| EP0498011B1 (de) | Neue Salze der 2-(2,6-Dichloranilino)-phenylessigsäure, Verfahren zu ihrer Herstellung und ihre Verwendung für topisch anwendbare pharmazeutische Zubereitungen | |
| DE2428201A1 (de) | Anthranilsaeurederivate, verfahren zu deren herstellung und diese derivate enthaltende arzneimittel | |
| DE3634989C2 (de) | Verfahren zur Herstellung von substituierten Bisphenolen | |
| DE2934166A1 (de) | 1,3-benzoxazin-2,4-dion-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE2607627A1 (de) | 1-0-acetoxybenzoyl-4-hydroxy-l-prolin sowie 1-0-acetoxybenzoyl-l-prolin, verfahren zu ihrer herstellung und ihre verwendung als medikament | |
| DE2839311C2 (de) | Pharmazeutisches Präparat gegen Geschwüre | |
| DE3706431C2 (en, 2012) | ||
| EP0036992B1 (de) | Verwendung von S-Benzyl-3-benzylthiopropionthioat in Arzneimitteln | |
| DE2065420A1 (de) | Arzneimittel enthaltend d-2-(methoxy2-naphthyl)-propanal | |
| DE2753768A1 (de) | Antiphologistisch wirkende arzneimittel | |
| DE2617592A1 (de) | Neue 2- eckige klammer auf 4-(3-oxo- oder -hydroxy-alkyl)-phenyl eckige klammer zu -alkansaeuren und deren nicht toxische salze, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |