IL90043A - Sulfonanilides, their preparation and pharmaceutical preparations containing them - Google Patents
Sulfonanilides, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL90043A IL90043A IL9004389A IL9004389A IL90043A IL 90043 A IL90043 A IL 90043A IL 9004389 A IL9004389 A IL 9004389A IL 9004389 A IL9004389 A IL 9004389A IL 90043 A IL90043 A IL 90043A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- tetrahydro
- ethyl
- hydroxy
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- -1 hydroxymethylene Chemical group 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
- LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000004615 ingredient Substances 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 206010020772 Hypertension Diseases 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- TXDMZGKDBWOUNK-UHFFFAOYSA-N n-[4-[2-(1,2,3,4-tetrahydronaphthalen-2-ylmethylamino)ethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNCC1CC2=CC=CC=C2CC1 TXDMZGKDBWOUNK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 238000001819 mass spectrum Methods 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
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- 230000036772 blood pressure Effects 0.000 description 11
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- 238000009472 formulation Methods 0.000 description 11
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 238000000746 purification Methods 0.000 description 9
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- VWANUORJXZCEKM-UHFFFAOYSA-N 3-[4-(methanesulfonamido)phenyl]propane-1-sulfonic acid Chemical compound CS(=O)(=O)NC1=CC=C(CCCS(O)(=O)=O)C=C1 VWANUORJXZCEKM-UHFFFAOYSA-N 0.000 description 8
- SYJXOXYLCUTLII-UHFFFAOYSA-N n-[4-[2-(dibenzylamino)acetyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(=O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 SYJXOXYLCUTLII-UHFFFAOYSA-N 0.000 description 8
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- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 150000003840 hydrochlorides Chemical class 0.000 description 6
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- WKQAFPKAFXIRCK-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-ylmethanamine Chemical compound C1=CC=C2CC(CN)CCC2=C1 WKQAFPKAFXIRCK-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- 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 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
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- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
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- WVKIDOVZHMZYMW-UHFFFAOYSA-N 3-(nitromethyl)-1,2-dihydronaphthalene Chemical compound C1=CC=C2CCC(C[N+](=O)[O-])=CC2=C1 WVKIDOVZHMZYMW-UHFFFAOYSA-N 0.000 description 3
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- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- ZDJMFTJPPKEEJN-UHFFFAOYSA-N n-[4-[2-(benzylamino)ethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNCC1=CC=CC=C1 ZDJMFTJPPKEEJN-UHFFFAOYSA-N 0.000 description 3
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- 101100136062 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) PE10 gene Proteins 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011461 current therapy Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- GHACVBCUANDNID-QFBILLFUSA-N n-[4-[(1s)-1-hydroxy-2-[[(2s)-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]methylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1[C@H](O)CNC[C@H]1C(=O)C2=CC=CC=C2CC1 GHACVBCUANDNID-QFBILLFUSA-N 0.000 description 1
- KAPZQBINCNUWLG-UHFFFAOYSA-N n-[4-[1-hydroxy-2-(1,2,3,4-tetrahydronaphthalen-2-ylmethylamino)ethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(O)CNCC1CC2=CC=CC=C2CC1 KAPZQBINCNUWLG-UHFFFAOYSA-N 0.000 description 1
- MAWQOLSQBRMGPH-UHFFFAOYSA-N n-[4-[2-(1,2,3,4-tetrahydronaphthalen-2-ylmethylamino)ethyl]phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)C)=CC=C1CCNCC1CC2=CC=CC=C2CC1 MAWQOLSQBRMGPH-UHFFFAOYSA-N 0.000 description 1
- APOOUNCOSKLROK-UHFFFAOYSA-N n-[4-[2-(dibenzylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 APOOUNCOSKLROK-UHFFFAOYSA-N 0.000 description 1
- HVXCMBVTLARCNV-UHFFFAOYSA-N n-[4-[2-[benzyl(1,2,3,4-tetrahydronaphthalen-2-ylmethyl)amino]acetyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(=O)CN(CC=1C=CC=CC=1)CC1CC2=CC=CC=C2CC1 HVXCMBVTLARCNV-UHFFFAOYSA-N 0.000 description 1
- WZBCIFZVBDLSDN-UHFFFAOYSA-N n-benzyl-1-phenylmethanamine;hydrobromide Chemical compound Br.C=1C=CC=CC=1CNCC1=CC=CC=C1 WZBCIFZVBDLSDN-UHFFFAOYSA-N 0.000 description 1
- UPHOVRVOOJDJEQ-UHFFFAOYSA-N n-phenyl-1,2,3,4-tetrahydronaphthalene-1-sulfonamide Chemical class C1CCC2=CC=CC=C2C1S(=O)(=O)NC1=CC=CC=C1 UPHOVRVOOJDJEQ-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888809314A GB8809314D0 (en) | 1988-04-20 | 1988-04-20 | Anti-hypertensive sulfonanilides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL90043A0 IL90043A0 (en) | 1989-12-15 |
| IL90043A true IL90043A (en) | 1995-01-24 |
Family
ID=10635507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9004389A IL90043A (en) | 1988-04-20 | 1989-04-19 | Sulfonanilides, their preparation and pharmaceutical preparations containing them |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5102914A (da) |
| EP (1) | EP0338793B1 (da) |
| JP (1) | JPH026461A (da) |
| KR (1) | KR890016002A (da) |
| AT (1) | ATE96429T1 (da) |
| AU (1) | AU626850B2 (da) |
| CA (1) | CA1332615C (da) |
| DE (1) | DE68910165T2 (da) |
| DK (1) | DK189089A (da) |
| ES (1) | ES2059737T3 (da) |
| FI (1) | FI91398C (da) |
| GB (1) | GB8809314D0 (da) |
| HU (1) | HU204028B (da) |
| IL (1) | IL90043A (da) |
| MC (1) | MC2027A1 (da) |
| MX (1) | MX9203218A (da) |
| MY (1) | MY105138A (da) |
| NO (1) | NO173010C (da) |
| NZ (1) | NZ228803A (da) |
| PH (1) | PH26179A (da) |
| PT (1) | PT90307B (da) |
| ZA (1) | ZA892880B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194450A (en) * | 1988-04-20 | 1993-03-16 | Burroughs Wellcome Co. | Anti-hypertensive sulfonanilides |
| US5360822A (en) * | 1990-02-07 | 1994-11-01 | Nippon Shinyaku Co. Ltd. | Sulfonanilide derivatives and medicine |
| EP0538469B1 (en) * | 1990-02-07 | 1995-09-27 | Nippon Shinyaku Company, Limited | Sulfonanilide derivative and medicine |
| GB9020695D0 (en) * | 1990-09-22 | 1990-11-07 | Wellcome Found | Anti-hypertensive tetralins |
| US5508306A (en) * | 1992-11-13 | 1996-04-16 | Synaptic Pharmaceutical Corporation | Aromatic amine derivatives |
| DE19604191A1 (de) * | 1996-02-06 | 1997-08-07 | Hoechst Schering Agrevo Gmbh | 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1962497C3 (de) * | 1969-12-12 | 1979-09-20 | C.H. Boehringer Sohn, 6507 Ingelheim | Naphthylalkyl- a -hydroxyphenäthyl-amine, ihre Herstellung und diese enthaltende Arzneimittel |
| US4044150A (en) * | 1976-06-18 | 1977-08-23 | Mead Johnson & Company | Antihypertensive 4'-[1-hydroxy-2-[(1-phenoxy ethyl)-amino]ethyl]methanesulfonanilide and salts thereof and therapeutic use |
| GB2185741B (en) * | 1986-01-27 | 1989-10-25 | American Home Prod | Heterocyclic sulphonamides |
| EG18188A (en) * | 1986-05-01 | 1992-09-30 | Pfizer Ltd | Process for preparation anti-arhythmia agents |
| DE3630903A1 (de) * | 1986-09-11 | 1988-03-24 | Thomae Gmbh Dr K | Neue tetrahydronaphthalin- und indanderivate, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| GB8707123D0 (en) * | 1987-03-25 | 1987-04-29 | Pfizer Ltd | Antiarrhythmic agents |
-
1988
- 1988-04-20 GB GB888809314A patent/GB8809314D0/en active Pending
-
1989
- 1989-04-19 KR KR1019890005237A patent/KR890016002A/ko not_active Application Discontinuation
- 1989-04-19 EP EP89303862A patent/EP0338793B1/en not_active Expired - Lifetime
- 1989-04-19 DE DE89303862T patent/DE68910165T2/de not_active Expired - Fee Related
- 1989-04-19 FI FI891866A patent/FI91398C/fi not_active IP Right Cessation
- 1989-04-19 AT AT89303862T patent/ATE96429T1/de not_active IP Right Cessation
- 1989-04-19 DK DK189089A patent/DK189089A/da not_active Application Discontinuation
- 1989-04-19 PH PH38532A patent/PH26179A/en unknown
- 1989-04-19 HU HU891909A patent/HU204028B/hu not_active IP Right Cessation
- 1989-04-19 NZ NZ228803A patent/NZ228803A/xx unknown
- 1989-04-19 ZA ZA892880A patent/ZA892880B/xx unknown
- 1989-04-19 MC MC892046A patent/MC2027A1/xx unknown
- 1989-04-19 MY MYPI89000502A patent/MY105138A/en unknown
- 1989-04-19 AU AU33221/89A patent/AU626850B2/en not_active Ceased
- 1989-04-19 ES ES89303862T patent/ES2059737T3/es not_active Expired - Lifetime
- 1989-04-19 PT PT90307A patent/PT90307B/pt not_active IP Right Cessation
- 1989-04-19 CA CA000597117A patent/CA1332615C/en not_active Expired - Fee Related
- 1989-04-19 NO NO891609A patent/NO173010C/no unknown
- 1989-04-19 IL IL9004389A patent/IL90043A/en unknown
- 1989-04-19 JP JP1097714A patent/JPH026461A/ja active Pending
- 1989-12-18 US US07/455,909 patent/US5102914A/en not_active Expired - Fee Related
-
1992
- 1992-06-24 MX MX9203218A patent/MX9203218A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI91398C (fi) | 1994-06-27 |
| FI891866A (fi) | 1989-10-21 |
| MY105138A (en) | 1994-08-30 |
| ZA892880B (en) | 1990-12-28 |
| HU204028B (en) | 1991-11-28 |
| EP0338793A3 (en) | 1991-01-02 |
| ES2059737T3 (es) | 1994-11-16 |
| AU626850B2 (en) | 1992-08-13 |
| PT90307A (pt) | 1989-11-10 |
| NO891609D0 (no) | 1989-04-19 |
| DE68910165D1 (de) | 1993-12-02 |
| PT90307B (pt) | 1994-09-30 |
| DK189089A (da) | 1989-10-21 |
| IL90043A0 (en) | 1989-12-15 |
| EP0338793A2 (en) | 1989-10-25 |
| NO173010B (no) | 1993-07-05 |
| DE68910165T2 (de) | 1994-04-28 |
| ATE96429T1 (de) | 1993-11-15 |
| EP0338793B1 (en) | 1993-10-27 |
| NO891609L (no) | 1989-10-23 |
| MC2027A1 (fr) | 1990-04-25 |
| FI91398B (fi) | 1994-03-15 |
| AU3322189A (en) | 1989-10-26 |
| US5102914A (en) | 1992-04-07 |
| DK189089D0 (da) | 1989-04-19 |
| KR890016002A (ko) | 1989-11-27 |
| JPH026461A (ja) | 1990-01-10 |
| GB8809314D0 (en) | 1988-05-25 |
| PH26179A (en) | 1992-03-18 |
| FI891866A0 (fi) | 1989-04-19 |
| NZ228803A (en) | 1992-01-29 |
| CA1332615C (en) | 1994-10-18 |
| NO173010C (no) | 1993-10-13 |
| MX9203218A (es) | 1992-07-01 |
| HUT51600A (en) | 1990-05-28 |
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