DE1917432C2 - 4-Hydroxythiazoline, deren Herstellung und Verwendung - Google Patents
4-Hydroxythiazoline, deren Herstellung und VerwendungInfo
- Publication number
- DE1917432C2 DE1917432C2 DE1917432A DE1917432A DE1917432C2 DE 1917432 C2 DE1917432 C2 DE 1917432C2 DE 1917432 A DE1917432 A DE 1917432A DE 1917432 A DE1917432 A DE 1917432A DE 1917432 C2 DE1917432 C2 DE 1917432C2
- Authority
- DE
- Germany
- Prior art keywords
- thiazoline
- phenyl
- acetic acid
- hydroxy
- chlorophenyl
- 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
- MKQGJQWDMGKYIS-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-4-ol Chemical class OC1CSC=N1 MKQGJQWDMGKYIS-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003557 thiazoles Chemical class 0.000 claims description 7
- 125000004799 bromophenyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- AIPANIYQEBQYGC-UHFFFAOYSA-N 4-bromobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(Br)C=C1 AIPANIYQEBQYGC-UHFFFAOYSA-N 0.000 claims description 2
- 241000700159 Rattus Species 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
- 206010030113 Oedema Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- MGDWUTQKXCZNAJ-UHFFFAOYSA-N ethyl 4-bromo-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CBr MGDWUTQKXCZNAJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000002769 thiazolinyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- -1 methoxyphenyl Chemical group 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- RRHNMHKZFWKJMQ-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-4-hydroxy-2-phenyl-5H-1,3-thiazol-5-yl]acetic acid Chemical compound ClC1=CC=C(C=C1)C1(N=C(SC1CC(=O)O)C1=CC=CC=C1)O RRHNMHKZFWKJMQ-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OUMFRNLNSWLXOS-UHFFFAOYSA-N 2-[4-(4-bromophenyl)-4-hydroxy-2-phenyl-5H-1,3-thiazol-5-yl]acetic acid Chemical compound BrC1=CC=C(C=C1)C1(N=C(SC1CC(=O)O)C1=CC=CC=C1)O OUMFRNLNSWLXOS-UHFFFAOYSA-N 0.000 description 4
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- IGOYRYSKKLREIH-UHFFFAOYSA-N 3-bromo-4-(4-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=C(Cl)C=C1 IGOYRYSKKLREIH-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical class OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- VLABNHFFOMCDKP-UHFFFAOYSA-N 2-[4-(4-bromophenyl)-2-phenyl-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Br)C=C1 VLABNHFFOMCDKP-UHFFFAOYSA-N 0.000 description 1
- JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 description 1
- YCFPBUQIMAENQR-UHFFFAOYSA-N 3-bromo-4-(4-bromophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=C(Br)C=C1 YCFPBUQIMAENQR-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- WKWVTPKUHJOVTI-UHFFFAOYSA-N 4-methoxybenzenecarbothioamide Chemical compound COC1=CC=C(C(N)=S)C=C1 WKWVTPKUHJOVTI-UHFFFAOYSA-N 0.000 description 1
- ZNOBVFDQOBGJRO-UHFFFAOYSA-N CC(C=CC=C1)=C1C(SC1CC(O)=O)=NC1(C1=CC=CC=C1)O Chemical compound CC(C=CC=C1)=C1C(SC1CC(O)=O)=NC1(C1=CC=CC=C1)O ZNOBVFDQOBGJRO-UHFFFAOYSA-N 0.000 description 1
- OEYVVTIZUIOVHX-UHFFFAOYSA-N COC1=CC=C(C2(N=C(C(C=C3)=CC=C3Cl)SC2CC(O)=O)O)C=C1 Chemical compound COC1=CC=C(C2(N=C(C(C=C3)=CC=C3Cl)SC2CC(O)=O)O)C=C1 OEYVVTIZUIOVHX-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- AIMRUBCYEXWCCE-UHFFFAOYSA-N S1C=NCC1CC(=O)O Chemical compound S1C=NCC1CC(=O)O AIMRUBCYEXWCCE-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/14—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB06909/68A GB1262292A (en) | 1968-04-09 | 1968-04-09 | Novel thiazoline derivatives, the preparation thereof and compositions containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1917432A1 DE1917432A1 (de) | 1969-11-06 |
| DE1917432C2 true DE1917432C2 (de) | 1983-10-06 |
Family
ID=10085871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1917432A Expired DE1917432C2 (de) | 1968-04-09 | 1969-04-03 | 4-Hydroxythiazoline, deren Herstellung und Verwendung |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US3607879A (en:Method) |
| AT (1) | AT306007B (en:Method) |
| BE (1) | BE731200A (en:Method) |
| CH (1) | CH513906A (en:Method) |
| CY (1) | CY800A (en:Method) |
| DE (1) | DE1917432C2 (en:Method) |
| DK (1) | DK138991C (en:Method) |
| FI (1) | FI54921C (en:Method) |
| FR (1) | FR2007419A1 (en:Method) |
| GB (1) | GB1262292A (en:Method) |
| IE (1) | IE32678B1 (en:Method) |
| IL (1) | IL31915A (en:Method) |
| LU (1) | LU58368A1 (en:Method) |
| MY (1) | MY7500115A (en:Method) |
| NL (1) | NL165160C (en:Method) |
| PL (1) | PL71273B1 (en:Method) |
| SE (1) | SE390635B (en:Method) |
| YU (2) | YU33959B (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5175065A (en:Method) * | 1974-12-06 | 1976-06-29 | Shionogi Seiyaku Kk | |
| GR74148B (en:Method) * | 1980-04-03 | 1984-06-06 | Wyeth John & Brother Ltd | |
| CN85102855B (zh) * | 1985-04-01 | 1987-09-23 | 曹培生 | 一种非线性电磁振动装置 |
| EP0934937B1 (en) | 1990-11-30 | 2002-02-27 | Otsuka Pharmaceutical Co., Ltd. | Azole derivatives as superoxide radical inhibitor |
| US5840739A (en) * | 1992-11-16 | 1998-11-24 | University Of Florida Research Foundation, Inc. | Thiazoline acid derivatives |
| MY128323A (en) * | 1996-09-30 | 2007-01-31 | Otsuka Pharma Co Ltd | Thiazole derivatives for inhibition of cytokine production and of cell adhesion |
| CA2318368C (en) | 1998-01-28 | 2007-09-11 | Shionogi & Co., Ltd. | Novel tricyclic compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3147273A (en) * | 1963-05-02 | 1964-09-01 | Upjohn Co | Certain 2h-isothiazolo [4, 5-b] indol-3 (4h)-one 1-oxide compounds and their preparation |
| NL130759C (en:Method) * | 1965-10-07 |
-
1968
- 1968-04-09 GB GB06909/68A patent/GB1262292A/en not_active Expired
- 1968-04-09 CY CY800A patent/CY800A/xx unknown
-
1969
- 1969-03-24 IE IE387/69A patent/IE32678B1/xx unknown
- 1969-03-26 IL IL31915A patent/IL31915A/en unknown
- 1969-03-31 AT AT315069A patent/AT306007B/de not_active IP Right Cessation
- 1969-04-03 DE DE1917432A patent/DE1917432C2/de not_active Expired
- 1969-04-03 FI FI985/69A patent/FI54921C/fi active
- 1969-04-04 LU LU58368D patent/LU58368A1/xx unknown
- 1969-04-07 YU YU871/69A patent/YU33959B/xx unknown
- 1969-04-08 FR FR6910756A patent/FR2007419A1/fr active Pending
- 1969-04-08 PL PL1969132832A patent/PL71273B1/pl unknown
- 1969-04-08 US US814445A patent/US3607879A/en not_active Expired - Lifetime
- 1969-04-08 US US814444A patent/US3621028A/en not_active Expired - Lifetime
- 1969-04-08 SE SE6904950A patent/SE390635B/xx unknown
- 1969-04-08 BE BE731200D patent/BE731200A/xx not_active IP Right Cessation
- 1969-04-08 DK DK192969A patent/DK138991C/da active
- 1969-04-09 CH CH538469A patent/CH513906A/de not_active IP Right Cessation
- 1969-04-09 NL NL6905474.A patent/NL165160C/xx not_active IP Right Cessation
-
1975
- 1975-12-30 MY MY115/75A patent/MY7500115A/xx unknown
-
1977
- 1977-05-20 YU YU1278/77A patent/YU39998B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH513906A (de) | 1971-10-15 |
| IE32678B1 (en) | 1973-10-31 |
| MY7500115A (en) | 1975-12-31 |
| IE32678L (en) | 1969-10-09 |
| YU127877A (en) | 1982-06-30 |
| AT306007B (de) | 1973-03-26 |
| YU39998B (en) | 1985-06-30 |
| FI54921C (fi) | 1979-04-10 |
| YU33959B (en) | 1978-09-08 |
| YU87169A (en) | 1978-02-28 |
| DE1917432A1 (de) | 1969-11-06 |
| NL6905474A (en:Method) | 1969-10-13 |
| DK138991C (da) | 1979-05-14 |
| IL31915A (en) | 1972-10-29 |
| GB1262292A (en) | 1972-02-02 |
| US3621028A (en) | 1971-11-16 |
| DK138991B (da) | 1978-11-27 |
| US3607879A (en) | 1971-09-21 |
| PL71273B1 (en:Method) | 1974-04-30 |
| NL165160C (nl) | 1981-03-16 |
| NL165160B (nl) | 1980-10-15 |
| BE731200A (en:Method) | 1969-10-08 |
| LU58368A1 (en:Method) | 1969-07-16 |
| FI54921B (fi) | 1978-12-29 |
| FR2007419A1 (en:Method) | 1970-01-09 |
| IL31915A0 (en) | 1969-05-28 |
| CY800A (en) | 1976-12-01 |
| SE390635B (sv) | 1977-01-03 |
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Ipc: C07D277/14 |
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Free format text: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. DR.JUR. DR.RER.NAT. MARX, L., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |