FI63230C - Foerfarande foer framstaellning av 4-hydroxi-3-(5-metyl-3-isoxazolylkarbamoyl)-3-metyl-2h-1,2-bensotiazin-1,1-dioxid samt vid foerfarandet anvaendbara mellanprodukter - Google Patents
Foerfarande foer framstaellning av 4-hydroxi-3-(5-metyl-3-isoxazolylkarbamoyl)-3-metyl-2h-1,2-bensotiazin-1,1-dioxid samt vid foerfarandet anvaendbara mellanprodukter Download PDFInfo
- Publication number
- FI63230C FI63230C FI761431A FI761431A FI63230C FI 63230 C FI63230 C FI 63230C FI 761431 A FI761431 A FI 761431A FI 761431 A FI761431 A FI 761431A FI 63230 C FI63230 C FI 63230C
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- Finland
- Prior art keywords
- methyl
- formula
- dioxide
- hydroxy
- compound
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- 238000000034 method Methods 0.000 title claims description 23
- -1 5-METHYL-3-ISOXAZOLYLCARBAMOYL Chemical class 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000020477 pH reduction Effects 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- YYUAYBYLJSNDCX-UHFFFAOYSA-N isoxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YYUAYBYLJSNDCX-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000012022 methylating agents Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000007069 methylation reaction Methods 0.000 claims description 4
- OCEZJTJAJHRHDA-UHFFFAOYSA-N n-(5-methyl-1,2-oxazol-3-yl)-2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetamide Chemical compound O1C(C)=CC(NC(=O)CN2S(C3=CC=CC=C3C2=O)(=O)=O)=N1 OCEZJTJAJHRHDA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- DXJICGSIRAJIDN-UHFFFAOYSA-N 2-chloro-N-(5-methyl-3-isoxazolyl)acetamide Chemical compound CC1=CC(NC(=O)CCl)=NO1 DXJICGSIRAJIDN-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000011987 methylation Effects 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229940081974 saccharin Drugs 0.000 claims description 2
- 235000019204 saccharin Nutrition 0.000 claims description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 2
- HKAXFLFYRNKEAB-UHFFFAOYSA-N 5-methyl-2h-1,3-oxazol-3-amine Chemical compound CC1=CN(N)CO1 HKAXFLFYRNKEAB-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006462 rearrangement reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JQVPAYCOPULQCA-UHFFFAOYSA-N 5-methyl-3h-1,2-oxazol-2-amine Chemical compound CC1=CCN(N)O1 JQVPAYCOPULQCA-UHFFFAOYSA-N 0.000 description 2
- USZQJPNAGRKYGD-UHFFFAOYSA-N CC(C1=NOC(C(NSC2=C3C=CC=C2)=C3O)=N1)=O Chemical compound CC(C1=NOC(C(NSC2=C3C=CC=C2)=C3O)=N1)=O USZQJPNAGRKYGD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YWXSCVWEJBLKTK-UHFFFAOYSA-N 2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-1lambda6,2-benzothiazine-3-carboxamide Chemical compound C=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YWXSCVWEJBLKTK-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
- PVNIYDCDHSFJTK-UHFFFAOYSA-N 2h-1,2-benzothiazin-4-ol Chemical compound C1=CC=C2C(O)=CNSC2=C1 PVNIYDCDHSFJTK-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- NBICRQSSKKUVNN-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical class C1=CC=C2S(=O)(=O)NC(C(=O)O)=C(O)C2=C1 NBICRQSSKKUVNN-UHFFFAOYSA-N 0.000 description 1
- VFFAIXJGMPMBBR-UHFFFAOYSA-N 4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-3H-1,2-benzothiazole-3-carboxamide Chemical compound OC1=CC=CC2=C1C(N(S2(=O)=O)C)C(=O)NC2=NOC(=C2)C VFFAIXJGMPMBBR-UHFFFAOYSA-N 0.000 description 1
- CEFGWFXVHFZNQW-UHFFFAOYSA-N 4-hydroxy-n-(1,2-oxazol-3-yl)-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical class N1S(=O)(=O)C2=CC=CC=C2C(O)=C1C(=O)NC=1C=CON=1 CEFGWFXVHFZNQW-UHFFFAOYSA-N 0.000 description 1
- AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010028116 Mucosal inflammation Diseases 0.000 description 1
- 201000010927 Mucositis Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GTPFFQKFSNQICB-UHFFFAOYSA-N N1(CCCC1)N.CN1S(C2=C(C(C1)=O)C=CC=C2)(=O)=O Chemical compound N1(CCCC1)N.CN1S(C2=C(C(C1)=O)C=CC=C2)(=O)=O GTPFFQKFSNQICB-UHFFFAOYSA-N 0.000 description 1
- IBOFHYROWRPMOZ-UHFFFAOYSA-N O1CCCCC1.CC1=CC(=NO1)NC(CN1SC2=C(C1=O)C=CC=C2)=O Chemical compound O1CCCCC1.CC1=CC(=NO1)NC(CN1SC2=C(C1=O)C=CC=C2)=O IBOFHYROWRPMOZ-UHFFFAOYSA-N 0.000 description 1
- UMXYGTDGRCRSBZ-UHFFFAOYSA-N OC1=C(N(SC2=C1C=CC=C2)C)C2=NC=NO2 Chemical compound OC1=C(N(SC2=C1C=CC=C2)C)C2=NC=NO2 UMXYGTDGRCRSBZ-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- KNYFJYVFUYERQR-UHFFFAOYSA-N methyl 2-(3-oxo-1,2-benzothiazol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OC)SC2=C1 KNYFJYVFUYERQR-UHFFFAOYSA-N 0.000 description 1
- GEUURTZIEGFZAG-UHFFFAOYSA-N methyl 4-hydroxy-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)NC(C(=O)OC)=C(O)C2=C1 GEUURTZIEGFZAG-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- MPWFKSJGIUHZOH-UHFFFAOYSA-N n-chloro-n-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound CC(=O)N(Cl)C=1C=C(C)ON=1 MPWFKSJGIUHZOH-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 1
- XGBOQPVRRBPDDF-UHFFFAOYSA-M sodium;urea;hydroxide Chemical compound [OH-].[Na+].NC(N)=O XGBOQPVRRBPDDF-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57756875 | 1975-05-21 | ||
| US05/577,568 US3957772A (en) | 1975-05-21 | 1975-05-21 | Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2h-1,2-benzothiazine 1,1-dioxide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI761431A7 FI761431A7 (enrdf_load_stackoverflow) | 1976-11-22 |
| FI63230B FI63230B (fi) | 1983-01-31 |
| FI63230C true FI63230C (fi) | 1983-05-10 |
Family
ID=24309281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI761431A FI63230C (fi) | 1975-05-21 | 1976-05-20 | Foerfarande foer framstaellning av 4-hydroxi-3-(5-metyl-3-isoxazolylkarbamoyl)-3-metyl-2h-1,2-bensotiazin-1,1-dioxid samt vid foerfarandet anvaendbara mellanprodukter |
Country Status (10)
| Country | Link |
|---|---|
| CH (1) | CH629802A5 (enrdf_load_stackoverflow) |
| DK (3) | DK148479C (enrdf_load_stackoverflow) |
| ES (1) | ES448088A1 (enrdf_load_stackoverflow) |
| FI (1) | FI63230C (enrdf_load_stackoverflow) |
| IE (1) | IE43102B1 (enrdf_load_stackoverflow) |
| IN (1) | IN143577B (enrdf_load_stackoverflow) |
| MX (1) | MX3139E (enrdf_load_stackoverflow) |
| NO (1) | NO145917C (enrdf_load_stackoverflow) |
| PH (2) | PH14848A (enrdf_load_stackoverflow) |
| SE (2) | SE429043B (enrdf_load_stackoverflow) |
-
1976
- 1976-03-30 IN IN548/CAL/76A patent/IN143577B/en unknown
- 1976-05-04 IE IE947/76A patent/IE43102B1/en unknown
- 1976-05-10 MX MX000219U patent/MX3139E/es unknown
- 1976-05-17 PH PH18443A patent/PH14848A/en unknown
- 1976-05-19 DK DK219876A patent/DK148479C/da active
- 1976-05-20 FI FI761431A patent/FI63230C/fi not_active IP Right Cessation
- 1976-05-20 SE SE7605752A patent/SE429043B/xx not_active IP Right Cessation
- 1976-05-20 ES ES448088A patent/ES448088A1/es not_active Expired
- 1976-05-20 NO NO761724A patent/NO145917C/no unknown
- 1976-05-21 CH CH642776A patent/CH629802A5/de not_active IP Right Cessation
-
1980
- 1980-01-22 DK DK25180A patent/DK149752C/da not_active IP Right Cessation
- 1980-01-22 DK DK25280A patent/DK148478C/da active
- 1980-03-03 SE SE8001649A patent/SE447112B/sv not_active IP Right Cessation
-
1981
- 1981-01-28 PH PH25141A patent/PH16804A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK149752B (da) | 1986-09-22 |
| NO761724L (enrdf_load_stackoverflow) | 1976-11-23 |
| DK148478C (da) | 1985-12-16 |
| SE8001649L (sv) | 1980-03-03 |
| PH16804A (en) | 1984-03-01 |
| SE7605752L (sv) | 1976-11-22 |
| ES448088A1 (es) | 1977-07-01 |
| IE43102B1 (en) | 1980-12-17 |
| DK25180A (da) | 1980-01-22 |
| DK25280A (da) | 1980-01-22 |
| NO145917C (no) | 1982-06-23 |
| CH629802A5 (en) | 1982-05-14 |
| SE447112B (sv) | 1986-10-27 |
| MX3139E (es) | 1980-05-06 |
| SE429043B (sv) | 1983-08-08 |
| DK148479C (da) | 1985-12-16 |
| FI761431A7 (enrdf_load_stackoverflow) | 1976-11-22 |
| FI63230B (fi) | 1983-01-31 |
| IE43102L (en) | 1976-11-21 |
| DK148478B (da) | 1985-07-15 |
| DK219876A (da) | 1976-11-22 |
| NO145917B (no) | 1982-03-15 |
| DK149752C (da) | 1987-03-16 |
| IN143577B (enrdf_load_stackoverflow) | 1977-12-31 |
| DK148479B (da) | 1985-07-15 |
| PH14848A (en) | 1982-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: WARNER-LAMBERT COMPANY |