CA1048025A - 4-hydroxy-2h-naphtho (2,1-e)-1,2-thiazine-3-carboxamide-1,1-dioxides, processes for their preparation and pharmaceuticals containing them - Google Patents
4-hydroxy-2h-naphtho (2,1-e)-1,2-thiazine-3-carboxamide-1,1-dioxides, processes for their preparation and pharmaceuticals containing themInfo
- Publication number
- CA1048025A CA1048025A CA239,175A CA239175A CA1048025A CA 1048025 A CA1048025 A CA 1048025A CA 239175 A CA239175 A CA 239175A CA 1048025 A CA1048025 A CA 1048025A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- naphtho
- dioxide
- thiazine
- hydroxy
- 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
- 238000000034 method Methods 0.000 title claims abstract description 49
- 230000008569 process Effects 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 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 title 1
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- -1 4-methylpyrid-2-yl Chemical group 0.000 claims description 81
- 238000006243 chemical reaction Methods 0.000 claims description 39
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 38
- 239000007858 starting material Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 17
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 17
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 17
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 15
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 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 claims description 9
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 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 claims description 5
- KCXSROUGMNGZKS-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-(4-methylpyridin-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=CC(C)=CC=N1 KCXSROUGMNGZKS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=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
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 230000008707 rearrangement Effects 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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- 229950011175 aminopicoline Drugs 0.000 claims description 3
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 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 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims 1
- JWQYUOFXHDXRLK-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-n-(1,3-thiazol-2-yl)-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound N1S(=O)(=O)C(C2=CC=CC=C2C=C2)=C2C(O)=C1C(=O)NC1=NC=CS1 JWQYUOFXHDXRLK-UHFFFAOYSA-N 0.000 claims 1
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- 239000004480 active ingredient Substances 0.000 description 22
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- AXTNEDXMBLSAIK-UHFFFAOYSA-N methyl 2-(1,1,3-trioxobenzo[g][1,2]benzothiazol-2-yl)acetate Chemical compound C1=CC=CC2=C(S(N(CC(=O)OC)C3=O)(=O)=O)C3=CC=C21 AXTNEDXMBLSAIK-UHFFFAOYSA-N 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
- 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 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
- CKBLINMLEQFGRW-UHFFFAOYSA-N n-(2-fluorophenyl)-4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound N1S(=O)(=O)C(C2=CC=CC=C2C=C2)=C2C(O)=C1C(=O)NC1=CC=CC=C1F CKBLINMLEQFGRW-UHFFFAOYSA-N 0.000 description 1
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- AFMXLJARGFAMCU-UHFFFAOYSA-N n-(3-chlorophenyl)-4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound N1S(=O)(=O)C(C2=CC=CC=C2C=C2)=C2C(O)=C1C(=O)NC1=CC=CC(Cl)=C1 AFMXLJARGFAMCU-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
- RTFFAFALSGILET-UHFFFAOYSA-N n-(3-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=CC(F)=C1 RTFFAFALSGILET-UHFFFAOYSA-N 0.000 description 1
- DLFKYTQTNFSQCD-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-thiazol-2-yl)-4-hydroxy-1,1-dioxo-2h-benzo[h][1,2]benzothiazine-3-carboxamide Chemical compound S1C(C)=C(C)N=C1NC(=O)C1=C(O)C2=CC=C(C=CC=C3)C3=C2S(=O)(=O)N1 DLFKYTQTNFSQCD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OERAQLMUAGRTRA-UHFFFAOYSA-N n-(5-ethyl-1,3-thiazol-2-yl)-4-hydroxy-1,1-dioxo-2h-benzo[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)N1 OERAQLMUAGRTRA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VHUZRCKOPCYPRG-UHFFFAOYSA-N n-(6-chloropyridazin-3-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=C(Cl)N=N1 VHUZRCKOPCYPRG-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 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
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 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
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229950005175 sudoxicam Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 238000001665 trituration 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (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 |
|---|---|
| CA1048025A true CA1048025A (en) | 1979-02-06 |
Family
ID=25767938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,175A Expired CA1048025A (en) | 1974-11-08 | 1975-11-07 | 4-hydroxy-2h-naphtho (2,1-e)-1,2-thiazine-3-carboxamide-1,1-dioxides, processes for their preparation and pharmaceuticals containing them |
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 |
-
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
-
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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