CH618976A5 - - Google Patents
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- Publication number
- CH618976A5 CH618976A5 CH1433075A CH1433075A CH618976A5 CH 618976 A5 CH618976 A5 CH 618976A5 CH 1433075 A CH1433075 A CH 1433075A CH 1433075 A CH1433075 A CH 1433075A CH 618976 A5 CH618976 A5 CH 618976A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- hydroxy
- naphtho
- thiazine
- dioxide
- Prior art date
Links
- -1 4-methyl-2-pyridyl Chemical group 0.000 claims description 89
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002844 melting Methods 0.000 description 96
- 230000008018 melting Effects 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 39
- 239000008096 xylene Substances 0.000 description 39
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 36
- 239000000126 substance Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 235000019441 ethanol Nutrition 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 238000012360 testing method Methods 0.000 description 18
- 206010030113 Oedema Diseases 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- 241000700159 Rattus Species 0.000 description 13
- YTGIZSFOHFCPAX-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxylate Chemical compound C1=CC=CC2=C(S(=O)(=O)N(C(C(=O)OC)=C3O)C)C3=CC=C21 YTGIZSFOHFCPAX-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000002776 aggregation Effects 0.000 description 9
- 238000004220 aggregation Methods 0.000 description 9
- 239000002808 molecular sieve Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- XMXLBDNVSIHRRA-UHFFFAOYSA-N 4,5-dimethyl-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1C XMXLBDNVSIHRRA-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 5
- JJDSGHBAXFTEHZ-UHFFFAOYSA-N 4-ethyl-1,3-thiazol-2-amine Chemical compound CCC1=CSC(N)=N1 JJDSGHBAXFTEHZ-UHFFFAOYSA-N 0.000 description 5
- QBODTUQSKJHYHL-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 QBODTUQSKJHYHL-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
- 208000009386 Experimental Arthritis Diseases 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 229920001436 collagen Polymers 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- XPDXICVHAINXCZ-UHFFFAOYSA-N 4-ethyl-5-methyl-1,3-thiazol-2-amine Chemical compound CCC=1N=C(N)SC=1C XPDXICVHAINXCZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 210000002683 foot Anatomy 0.000 description 4
- 210000000548 hind-foot Anatomy 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000013558 reference substance Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 230000003313 weakening effect Effects 0.000 description 4
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 3
- LAJBHYQNKJCOLN-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-(4-methyl-1,3-thiazol-2-yl)-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC(C)=CS1 LAJBHYQNKJCOLN-UHFFFAOYSA-N 0.000 description 3
- FHHIPSIIRBMAFM-UHFFFAOYSA-N 5-ethyl-4-methyl-1,3-thiazol-2-amine Chemical compound CCC=1SC(N)=NC=1C FHHIPSIIRBMAFM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002322 anti-exudative effect Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- SMWAOXCEPHEGFV-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine Chemical compound C1CCCC2=C1N=C(N)S2 SMWAOXCEPHEGFV-UHFFFAOYSA-N 0.000 description 2
- HNOGSSUZDLBROJ-UHFFFAOYSA-N 5-ethyl-1,3-thiazol-2-amine Chemical compound CCC1=CN=C(N)S1 HNOGSSUZDLBROJ-UHFFFAOYSA-N 0.000 description 2
- GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 2
- ZIWHJKWMCYAKSY-UHFFFAOYSA-N 6,7-dihydro-2h-thiopyrano[4,3-d][1,3]thiazol-2-amine Chemical compound S1CCC2=NC(N)SC2=C1 ZIWHJKWMCYAKSY-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- GWFWYUROEMELNB-UHFFFAOYSA-N methyl 4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxylate Chemical compound C1=CC=CC2=C(S(=O)(=O)NC(C(=O)OC)=C3O)C3=CC=C21 GWFWYUROEMELNB-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- PJFNCKCWQXWTKK-UHFFFAOYSA-N n-(4-fluorophenyl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=C(F)C=C1 PJFNCKCWQXWTKK-UHFFFAOYSA-N 0.000 description 2
- LFTZVAOUJIOJOL-UHFFFAOYSA-N n-(6-chloropyrazin-2-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=CN=CC(Cl)=N1 LFTZVAOUJIOJOL-UHFFFAOYSA-N 0.000 description 2
- LPGLMCHRGVRMBT-UHFFFAOYSA-N n-(6-chloropyrimidin-4-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC(Cl)=NC=N1 LPGLMCHRGVRMBT-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical compound NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical compound NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
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- XQCIQOUFXISHEX-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical class C1=CC=CC2=C(S(=O)(=O)NC(C(=O)N)=C3O)C3=CC=C21 XQCIQOUFXISHEX-UHFFFAOYSA-N 0.000 description 1
- NRDPSKZHWRVTNY-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-4-ylbenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=NC=C1 NRDPSKZHWRVTNY-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- DZUMDMPDUGQAJV-UHFFFAOYSA-N butyl 4-hydroxy-2-methylbenzo[h][1,2]benzothiazine-3-carboxylate Chemical compound C1=CC=CC2=C(SN(C(C(=O)OCCCC)=C3O)C)C3=CC=C21 DZUMDMPDUGQAJV-UHFFFAOYSA-N 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LSZNARWCHDJJSU-UHFFFAOYSA-N ethyl 4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxylate Chemical compound C1=CC=CC2=C(S(=O)(=O)N(C(C(=O)OCC)=C3O)C)C3=CC=C21 LSZNARWCHDJJSU-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
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- 238000004817 gas chromatography Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 230000002503 metabolic effect Effects 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- LOAZYARIOUARRJ-UHFFFAOYSA-N methyl 2-ethyl-4-hydroxy-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxylate Chemical compound C1=CC=CC2=C(S(N(CC)C(C(=O)OC)=C3O)(=O)=O)C3=CC=C21 LOAZYARIOUARRJ-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- JTXOCMVTCWMPRD-UHFFFAOYSA-N n-(3-bromophenyl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC(Br)=C1 JTXOCMVTCWMPRD-UHFFFAOYSA-N 0.000 description 1
- NCASYMYRCUGUDM-UHFFFAOYSA-N n-(3-chlorophenyl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC(Cl)=C1 NCASYMYRCUGUDM-UHFFFAOYSA-N 0.000 description 1
- BAOANMOQOJQJEX-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-thiazol-2-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=C3C=CC=CC3=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC(C)=C(C)S1 BAOANMOQOJQJEX-UHFFFAOYSA-N 0.000 description 1
- BDTIHSAWNOCEQY-UHFFFAOYSA-N n-(4-ethyl-1,3-thiazol-2-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound CCC1=CSC(NC(=O)C=2N(S(=O)(=O)C3=C4C=CC=CC4=CC=C3C=2O)C)=N1 BDTIHSAWNOCEQY-UHFFFAOYSA-N 0.000 description 1
- NDEZFGPMHQZBMQ-UHFFFAOYSA-N n-(4-ethyl-5-methyl-1,3-thiazol-2-yl)-4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound S1C(C)=C(CC)N=C1NC(=O)C1=C(O)C2=CC=C(C=CC=C3)C3=C2S(=O)(=O)N1 NDEZFGPMHQZBMQ-UHFFFAOYSA-N 0.000 description 1
- BDXUHPUDRXHHPC-UHFFFAOYSA-N n-(4-ethyl-5-methyl-1,3-thiazol-2-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound S1C(C)=C(CC)N=C1NC(=O)C1=C(O)C2=CC=C(C=CC=C3)C3=C2S(=O)(=O)N1C BDXUHPUDRXHHPC-UHFFFAOYSA-N 0.000 description 1
- CXZGQOFXFNJTDJ-UHFFFAOYSA-N n-(5-ethyl-1,3-thiazol-2-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound S1C(CC)=CN=C1NC(=O)C1=C(O)C2=CC=C(C=CC=C3)C3=C2S(=O)(=O)N1C CXZGQOFXFNJTDJ-UHFFFAOYSA-N 0.000 description 1
- XWNOJDNFQIIUTR-UHFFFAOYSA-N n-(5-ethyl-4-methyl-1,3-thiazol-2-yl)-4-hydroxy-2-methyl-1,1-dioxobenzo[h][1,2]benzothiazine-3-carboxamide Chemical compound CC1=C(CC)SC(NC(=O)C=2N(S(=O)(=O)C3=C4C=CC=CC4=CC=C3C=2O)C)=N1 XWNOJDNFQIIUTR-UHFFFAOYSA-N 0.000 description 1
- WZHLTAVTOOSNPO-UHFFFAOYSA-N n-(6,7-dihydro-2h-thiopyrano[4,3-d][1,3]thiazol-2-yl)-4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound S1C2=CSCCC2=NC1NC(=O)C1=C(O)C(C=CC=2C3=CC=CC=2)=C3S(=O)(=O)N1 WZHLTAVTOOSNPO-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229950005175 sudoxicam Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742452996 DE2452996A1 (de) | 1974-11-08 | 1974-11-08 | Neue 4-hydroxy-2h-naphtho- eckige klammer auf 2,1-e eckige klammer zu -1,2thiazin-3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DE2539112A DE2539112C2 (de) | 1975-09-03 | 1975-09-03 | 4-Hydroxy-2H-naphtho[2,1-e]-1,2-thiazin-3-carboxamid-1,1-dioxide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618976A5 true CH618976A5 (en, 2012) | 1980-08-29 |
Family
ID=25767938
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1433075A CH618976A5 (en, 2012) | 1974-11-08 | 1975-11-05 | |
| CH198880A CH628040A5 (de) | 1974-11-08 | 1980-03-13 | Verfahren zur herstellung neuer 4-hydroxy-2h-naphtho(2,1-e)-1,2-thiazin-3-carboxamid-1,1-dioxyde. |
| CH198980A CH628041A5 (de) | 1974-11-08 | 1980-03-13 | Verfahren zur herstellung neuer 4-hydroxy-2h-naphtho(2,1-e)-1,2-thiazin-3-carboxamid-1,1-dioxyde. |
| CH199080A CH626080A5 (en, 2012) | 1974-11-08 | 1980-03-13 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH198880A CH628040A5 (de) | 1974-11-08 | 1980-03-13 | Verfahren zur herstellung neuer 4-hydroxy-2h-naphtho(2,1-e)-1,2-thiazin-3-carboxamid-1,1-dioxyde. |
| CH198980A CH628041A5 (de) | 1974-11-08 | 1980-03-13 | Verfahren zur herstellung neuer 4-hydroxy-2h-naphtho(2,1-e)-1,2-thiazin-3-carboxamid-1,1-dioxyde. |
| CH199080A CH626080A5 (en, 2012) | 1974-11-08 | 1980-03-13 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3992535A (en, 2012) |
| JP (1) | JPS51125292A (en, 2012) |
| AT (1) | AT345847B (en, 2012) |
| BG (1) | BG32715A3 (en, 2012) |
| CA (1) | CA1048025A (en, 2012) |
| CH (4) | CH618976A5 (en, 2012) |
| CS (1) | CS185583B2 (en, 2012) |
| DD (1) | DD122823A5 (en, 2012) |
| DK (1) | DK140533B (en, 2012) |
| ES (5) | ES442074A1 (en, 2012) |
| FI (1) | FI60011C (en, 2012) |
| FR (1) | FR2290211A1 (en, 2012) |
| GB (1) | GB1485910A (en, 2012) |
| HU (1) | HU174520B (en, 2012) |
| IE (1) | IE42930B1 (en, 2012) |
| IL (1) | IL48439A (en, 2012) |
| LU (1) | LU73748A1 (en, 2012) |
| NL (1) | NL7512271A (en, 2012) |
| NO (1) | NO143317C (en, 2012) |
| NZ (1) | NZ179178A (en, 2012) |
| PH (1) | PH11809A (en, 2012) |
| PL (1) | PL107647B1 (en, 2012) |
| RO (1) | RO68500A (en, 2012) |
| SE (1) | SE420605B (en, 2012) |
| SU (1) | SU575027A3 (en, 2012) |
| YU (1) | YU281075A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704485A1 (de) * | 1977-02-03 | 1978-08-10 | Thomae Gmbh Dr K | Neue 2,5-dihydro-1,2-thiazino eckige klammer auf 5,6-b eckige klammer zu indol-3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| IN158333B (en, 2012) * | 1981-08-03 | 1986-10-18 | Pfizer | |
| EP0082217A1 (de) * | 1981-12-23 | 1983-06-29 | Ciba-Geigy Ag | Neue Ammoniumsalze, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate und ihre Verwendung |
| US4683306A (en) * | 1984-07-13 | 1987-07-28 | Yuhan Corporation Co., Ltd. | Process for the preparation of 3,4-dihydro-2-substituted-2H-1,2-thiazine-carboxylic acid 1,1-dioxide derivatives |
| KR101855195B1 (ko) * | 2010-07-09 | 2018-05-08 | 액티브 바이오테크 에이비 | 퀴놀린-3-카르복사미드의 제조 방법 |
| CN103275035B (zh) * | 2013-06-28 | 2014-11-26 | 安徽中医学院 | 苯并噻嗪类化合物、其制备方法及其抗肿瘤用途 |
| USD825997S1 (en) | 2018-03-22 | 2018-08-21 | Remson Concepts, Inc | Stackable serving tray |
| USD835467S1 (en) | 2018-07-23 | 2018-12-11 | Remson Concepts, Inc. | Stackable serving tray |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1090252A (en) * | 1965-04-13 | 1967-11-08 | Ici Ltd | Dibenzothiazine derivatives |
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1975
- 1975-10-07 AT AT764875A patent/AT345847B/de not_active IP Right Cessation
- 1975-10-20 NL NL7512271A patent/NL7512271A/xx not_active Application Discontinuation
- 1975-10-24 ES ES442074A patent/ES442074A1/es not_active Expired
- 1975-10-29 US US05/626,623 patent/US3992535A/en not_active Expired - Lifetime
- 1975-10-29 SU SU7502183260A patent/SU575027A3/ru active
- 1975-10-31 GB GB45407/75A patent/GB1485910A/en not_active Expired
- 1975-11-03 RO RO7583800A patent/RO68500A/ro unknown
- 1975-11-03 BG BG031394A patent/BG32715A3/xx unknown
- 1975-11-04 CS CS7500007427A patent/CS185583B2/cs unknown
- 1975-11-05 HU HU75TO1014A patent/HU174520B/hu unknown
- 1975-11-05 PH PH17738A patent/PH11809A/en unknown
- 1975-11-05 CH CH1433075A patent/CH618976A5/de not_active IP Right Cessation
- 1975-11-06 YU YU02810/75A patent/YU281075A/xx unknown
- 1975-11-06 DD DD189304A patent/DD122823A5/xx unknown
- 1975-11-06 LU LU73748A patent/LU73748A1/xx unknown
- 1975-11-07 FR FR7534140A patent/FR2290211A1/fr active Granted
- 1975-11-07 FI FI753124A patent/FI60011C/fi not_active IP Right Cessation
- 1975-11-07 NZ NZ179178A patent/NZ179178A/xx unknown
- 1975-11-07 JP JP50133182A patent/JPS51125292A/ja active Pending
- 1975-11-07 IE IE2439/79A patent/IE42930B1/en unknown
- 1975-11-07 NO NO753738A patent/NO143317C/no unknown
- 1975-11-07 IL IL48439A patent/IL48439A/xx unknown
- 1975-11-07 PL PL1975184576A patent/PL107647B1/pl unknown
- 1975-11-07 DK DK503075AA patent/DK140533B/da not_active IP Right Cessation
- 1975-11-07 CA CA239,175A patent/CA1048025A/en not_active Expired
- 1975-11-07 SE SE7512534A patent/SE420605B/xx unknown
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1976
- 1976-09-25 ES ES451867A patent/ES451867A1/es not_active Expired
- 1976-09-25 ES ES451869A patent/ES451869A1/es not_active Expired
- 1976-09-25 ES ES451868A patent/ES451868A1/es not_active Expired
- 1976-09-25 ES ES451865A patent/ES451865A1/es not_active Expired
-
1980
- 1980-03-13 CH CH198880A patent/CH628040A5/de not_active IP Right Cessation
- 1980-03-13 CH CH198980A patent/CH628041A5/de not_active IP Right Cessation
- 1980-03-13 CH CH199080A patent/CH626080A5/de not_active IP Right Cessation
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