DE2331246A1 - Antiinflammatorisch wirksame thiazolabkoemmlinge und diese enthaltende arzneipraeparate - Google Patents
Antiinflammatorisch wirksame thiazolabkoemmlinge und diese enthaltende arzneipraeparateInfo
- Publication number
- DE2331246A1 DE2331246A1 DE2331246A DE2331246A DE2331246A1 DE 2331246 A1 DE2331246 A1 DE 2331246A1 DE 2331246 A DE2331246 A DE 2331246A DE 2331246 A DE2331246 A DE 2331246A DE 2331246 A1 DE2331246 A1 DE 2331246A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- compound
- alkyl group
- low molecular
- 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
- 238000002360 preparation method Methods 0.000 title claims description 16
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 12
- 239000002674 ointment Substances 0.000 claims description 8
- XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical compound NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 claims description 8
- 239000003826 tablet Substances 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- -1 methoxyethyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000006187 pill Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 6
- 150000001450 anions Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 description 28
- 241000700159 Rattus Species 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
- 235000010418 carrageenan Nutrition 0.000 description 19
- 229920001525 carrageenan Polymers 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 210000002683 foot Anatomy 0.000 description 12
- 210000000548 hind-foot Anatomy 0.000 description 11
- WPCSNGBKVXKBPU-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazole Chemical class C1=CSC(C=2C=NC=CC=2)=N1 WPCSNGBKVXKBPU-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000007979 thiazole derivatives Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 206010018691 Granuloma Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 description 5
- 239000002260 anti-inflammatory agent Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 235000019271 petrolatum Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 231100001274 therapeutic index Toxicity 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 230000033687 granuloma formation Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- GSKRSZFKXSINJN-UHFFFAOYSA-N n,n,4-trimethyl-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)N(C)C)SC(C=2C=NC=CC=2)=N1 GSKRSZFKXSINJN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 2
- HBJDUHQKKNYAAU-UHFFFAOYSA-N 4-phenyl-n-propan-2-yl-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CC(C)NC(=O)C=1SC(C=2C=NC=CC=2)=NC=1C1=CC=CC=C1 HBJDUHQKKNYAAU-UHFFFAOYSA-N 0.000 description 2
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 229940125851 compound 27 Drugs 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006194 liquid suspension Substances 0.000 description 2
- 239000010871 livestock manure Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- KJAHXHRALOUIDJ-UHFFFAOYSA-N n,n-dimethyl-4-phenyl-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CN(C)C(=O)C=1SC(C=2C=NC=CC=2)=NC=1C1=CC=CC=C1 KJAHXHRALOUIDJ-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 description 1
- QJACRCAPQIYMIH-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)C(Cl)C(C)=O QJACRCAPQIYMIH-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- UPBCYPSBQXICFZ-UHFFFAOYSA-N acetic acid;2-pyridin-3-yl-1,3-thiazole Chemical class CC(O)=O.C1=CSC(C=2C=NC=CC=2)=N1 UPBCYPSBQXICFZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VJJVNHGWVIRYGZ-UHFFFAOYSA-N bis(1,3-thiazol-5-yl)methanone Chemical compound C=1N=CSC=1C(=O)C1=CN=CS1 VJJVNHGWVIRYGZ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VRARBAPDHXBMFE-UHFFFAOYSA-N ethyl 4-phenyl-2-pyridin-3-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=NC=CC=2)=NC=1C1=CC=CC=C1 VRARBAPDHXBMFE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 230000010925 negative regulation of granuloma formation Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00264817A US3852293A (en) | 1972-06-21 | 1972-06-21 | 4-phenyl-2-(3-pyridyl)-thiazole carboxamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2331246A1 true DE2331246A1 (de) | 1974-01-17 |
Family
ID=23007730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2331246A Pending DE2331246A1 (de) | 1972-06-21 | 1973-06-19 | Antiinflammatorisch wirksame thiazolabkoemmlinge und diese enthaltende arzneipraeparate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3852293A (OSRAM) |
| JP (1) | JPS4949969A (OSRAM) |
| CA (1) | CA1023364A (OSRAM) |
| DE (1) | DE2331246A1 (OSRAM) |
| FR (1) | FR2189064B1 (OSRAM) |
| GB (1) | GB1437136A (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293549A (en) | 1977-11-07 | 1981-10-06 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktion-Saktieselskab) | Quinolinyl guanidines having antiinflammatory, analgesic or antipyretic activity |
| EP0045281A1 (de) * | 1980-07-28 | 1982-02-03 | Ciba-Geigy Ag | Thiazolinderivate und Verfahren zu ihrer Herstellung |
| US20100292236A1 (en) * | 2007-07-19 | 2010-11-18 | H. Lundbeck A/S | 5-Membered Heterocyclic Amides And Related Compounds |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4528291A (en) * | 1982-06-22 | 1985-07-09 | Schering Corporation | 2-(4'-Pyridinyl)-thiazole compounds and their use in increasing cardiac contractility |
| US4571402A (en) * | 1982-06-22 | 1986-02-18 | Schering Corporation | Anti-bronchoconstriction 2-(4'-pyridinyl)-thiazole derivatives, composition, and method of use therefor |
| SG86971A1 (en) * | 1990-11-30 | 2002-03-19 | Teijin Ltd | 2-arylthiazole derivatives and pharmaceutical composition thereof |
| JP2001517666A (ja) * | 1997-09-23 | 2001-10-09 | 藤沢薬品工業株式会社 | チアゾール誘導体 |
| EP2363396A1 (en) | 2001-06-11 | 2011-09-07 | Virochem Pharma Inc. | Thiophene derivatives as antiviral agents for flavivirus infection |
| US6936629B2 (en) * | 2001-12-21 | 2005-08-30 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of flavivirus infections |
| DE102004051277A1 (de) * | 2004-10-21 | 2006-04-27 | Merck Patent Gmbh | Heterocyclische Carbonylverbindungen |
| KR101394245B1 (ko) * | 2005-12-30 | 2014-05-14 | 에스케이바이오팜 주식회사 | 아이속사졸 유도체 및 이의 용도 |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | チオフェンおよびホスファチジルイノシトール３−キナーゼ（ｐｉ３ｋ）阻害薬としてのその使用 |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| EP2391619A1 (en) | 2009-01-30 | 2011-12-07 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| AU2011232347B2 (en) * | 2010-03-24 | 2015-08-06 | Musc Foundation For Research Development | Compositions and methods for the treatment of degenerative diseases |
| WO2012021615A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| NZ607087A (en) | 2010-08-11 | 2015-05-29 | Millennium Pharm Inc | Heteroaryls as inhibitors of pi3k and for the treatment of proliferative, inflammatory, or cardiovascular disorders |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012051410A2 (en) | 2010-10-13 | 2012-04-19 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CN102516239B (zh) * | 2011-12-13 | 2015-02-18 | 华东师范大学 | 一种芳香基噻唑类化合物及其类似物、用途及其制备方法 |
| US20140275178A1 (en) * | 2013-03-13 | 2014-09-18 | Musc Foundation For Research Development | Thiazole compounds, compositions and methods for treatment of degenerative diseases and disorders |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3705153A (en) * | 1969-05-14 | 1972-12-05 | Sumitomo Chemical Co | Novel thiazolyacetic acids and salts thereof |
-
1972
- 1972-06-21 US US00264817A patent/US3852293A/en not_active Expired - Lifetime
-
1973
- 1973-02-21 CA CA164,251A patent/CA1023364A/en not_active Expired
- 1973-06-15 GB GB2862373A patent/GB1437136A/en not_active Expired
- 1973-06-19 DE DE2331246A patent/DE2331246A1/de active Pending
- 1973-06-21 FR FR7322612A patent/FR2189064B1/fr not_active Expired
- 1973-06-21 JP JP48070413A patent/JPS4949969A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293549A (en) | 1977-11-07 | 1981-10-06 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktion-Saktieselskab) | Quinolinyl guanidines having antiinflammatory, analgesic or antipyretic activity |
| EP0045281A1 (de) * | 1980-07-28 | 1982-02-03 | Ciba-Geigy Ag | Thiazolinderivate und Verfahren zu ihrer Herstellung |
| US4406905A (en) | 1980-07-28 | 1983-09-27 | Ciba-Geigy Corporation | 2-Pyridyl-2-thiazoline-4-carboxylic acid derivatives |
| US20100292236A1 (en) * | 2007-07-19 | 2010-11-18 | H. Lundbeck A/S | 5-Membered Heterocyclic Amides And Related Compounds |
| US9133204B2 (en) | 2007-07-19 | 2015-09-15 | H. Lundbeck A/S | 5-membered heterocyclic amides and related compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2189064B1 (OSRAM) | 1977-04-15 |
| US3852293A (en) | 1974-12-03 |
| GB1437136A (en) | 1976-05-26 |
| CA1023364A (en) | 1977-12-27 |
| JPS4949969A (OSRAM) | 1974-05-15 |
| FR2189064A1 (OSRAM) | 1974-01-25 |
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