DE2630637C2 - Sulfamylbenzylaminderivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten - Google Patents
Sulfamylbenzylaminderivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthaltenInfo
- Publication number
- DE2630637C2 DE2630637C2 DE2630637A DE2630637A DE2630637C2 DE 2630637 C2 DE2630637 C2 DE 2630637C2 DE 2630637 A DE2630637 A DE 2630637A DE 2630637 A DE2630637 A DE 2630637A DE 2630637 C2 DE2630637 C2 DE 2630637C2
- Authority
- DE
- Germany
- Prior art keywords
- benzyl
- phenoxy
- formula
- sulfamylbenzyl
- compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 89
- 238000000034 method Methods 0.000 title claims description 43
- 238000002360 preparation method Methods 0.000 title claims description 33
- 239000003814 drug Substances 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 4
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 92
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 55
- 150000001412 amines Chemical class 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000011946 reduction process Methods 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- YFQFGDKUFNMHSK-UHFFFAOYSA-N 5-(anilinomethyl)-3-(butylamino)-2-phenoxybenzenesulfonamide Chemical compound C=1C(S(N)(=O)=O)=C(OC=2C=CC=CC=2)C(NCCCC)=CC=1CNC1=CC=CC=C1 YFQFGDKUFNMHSK-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- SNDJQZJVYFIGJW-UHFFFAOYSA-N 3-(butylamino)-2-phenoxy-5-[(pyridin-2-ylmethylamino)methyl]benzenesulfonamide Chemical compound C=1C(S(N)(=O)=O)=C(OC=2C=CC=CC=2)C(NCCCC)=CC=1CNCC1=CC=CC=N1 SNDJQZJVYFIGJW-UHFFFAOYSA-N 0.000 claims description 2
- IPURJCNMYJMYNC-UHFFFAOYSA-N 5-(aminomethyl)-2-phenoxy-3-[[2-(thiophen-2-ylmethylamino)phenyl]methyl]benzenesulfonamide Chemical compound O(C1=CC=CC=C1)C1=C(C=C(CN)C=C1S(N)(=O)=O)CC1=C(C=CC=C1)NCC1=CC=CS1 IPURJCNMYJMYNC-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 claims 1
- 241001091551 Clio Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 111
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 82
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 54
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 34
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000004519 manufacturing process Methods 0.000 description 25
- 238000001914 filtration Methods 0.000 description 22
- 238000001953 recrystallisation Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 20
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 235000011054 acetic acid Nutrition 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 210000003298 dental enamel Anatomy 0.000 description 10
- 239000012258 stirred mixture Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 150000003939 benzylamines Chemical class 0.000 description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 8
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- LLEXFZAWSJRTFT-UHFFFAOYSA-N 5-(aminomethyl)-3-(butylamino)-2-phenoxybenzenesulfonamide Chemical compound CCCCNC1=CC(CN)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 LLEXFZAWSJRTFT-UHFFFAOYSA-N 0.000 description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JCNMJXCBSLOHTP-UHFFFAOYSA-N 2-benzyl-5-(hydroxymethyl)-3-methylsulfanylbenzenesulfonamide Chemical compound CSC1=CC(CO)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 JCNMJXCBSLOHTP-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000001882 diuretic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- MRHNHRJQWICSPX-UHFFFAOYSA-N 2-benzyl-3-butoxy-5-[(dimethylamino)methyl]aniline Chemical compound CCCCOC1=CC(CN(C)C)=CC(N)=C1CC1=CC=CC=C1 MRHNHRJQWICSPX-UHFFFAOYSA-N 0.000 description 3
- OFPVARHUVOETPM-UHFFFAOYSA-N 2-benzyl-3-butoxy-5-[(dimethylamino)methyl]benzenesulfonamide Chemical compound CCCCOC1=CC(CN(C)C)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 OFPVARHUVOETPM-UHFFFAOYSA-N 0.000 description 3
- AESZWBMQUKQQNE-UHFFFAOYSA-N 3-(bromomethyl)benzenesulfonamide;hydrobromide Chemical compound Br.NS(=O)(=O)C1=CC=CC(CBr)=C1 AESZWBMQUKQQNE-UHFFFAOYSA-N 0.000 description 3
- BEBMBAOAFUFSMX-UHFFFAOYSA-N 3-(butylamino)-4-phenoxy-5-sulfamoylbenzamide Chemical compound CCCCNC1=CC(C(N)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 BEBMBAOAFUFSMX-UHFFFAOYSA-N 0.000 description 3
- BKMPCDQBTCOLCG-UHFFFAOYSA-N 3-amino-2-benzyl-5-(hydroxymethyl)benzenesulfonamide Chemical compound NC1=CC(CO)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 BKMPCDQBTCOLCG-UHFFFAOYSA-N 0.000 description 3
- NYXGWHUICJWIRE-UHFFFAOYSA-N 5-(hydroxymethyl)-3-(methylamino)-2-phenoxybenzenesulfonamide Chemical compound CNC1=CC(CO)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 NYXGWHUICJWIRE-UHFFFAOYSA-N 0.000 description 3
- FEQWCJKHPOSUGE-UHFFFAOYSA-N 5-[(benzylamino)methyl]-3-(butylamino)-2-phenoxybenzenesulfonamide Chemical compound C=1C(S(N)(=O)=O)=C(OC=2C=CC=CC=2)C(NCCCC)=CC=1CNCC1=CC=CC=C1 FEQWCJKHPOSUGE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 208000004880 Polyuria Diseases 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- ZYCMDWDFIQDPLP-UHFFFAOYSA-N hbr bromine Chemical compound Br.Br ZYCMDWDFIQDPLP-UHFFFAOYSA-N 0.000 description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- QYTCIAPAXXEVGE-UHFFFAOYSA-N (3-amino-4-benzyl-5-butoxyphenyl)methanol Chemical compound CCCCOC1=CC(CO)=CC(N)=C1CC1=CC=CC=C1 QYTCIAPAXXEVGE-UHFFFAOYSA-N 0.000 description 2
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 2
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WFNLWXRHDHDNRP-UHFFFAOYSA-N 2-benzyl-3-(benzylamino)-5-[(dimethylamino)methyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1CC=1C(S(N)(=O)=O)=CC(CN(C)C)=CC=1NCC1=CC=CC=C1 WFNLWXRHDHDNRP-UHFFFAOYSA-N 0.000 description 2
- MXUPZKGHJAVJDO-UHFFFAOYSA-N 2-benzyl-3-(butylamino)-5-[(dimethylamino)methyl]benzenesulfonamide Chemical compound CCCCNC1=CC(CN(C)C)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 MXUPZKGHJAVJDO-UHFFFAOYSA-N 0.000 description 2
- OLUAVXCRQVYJBS-UHFFFAOYSA-N 2-benzyl-3-butoxy-5-[[2-(diethylamino)ethylamino]methyl]benzenesulfonamide Chemical compound CCCCOC1=CC(CNCCN(CC)CC)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 OLUAVXCRQVYJBS-UHFFFAOYSA-N 0.000 description 2
- VTHLYRYVJCGRBR-UHFFFAOYSA-N 2-benzyl-5-(bromomethyl)-3-butoxyaniline;hydrobromide Chemical compound Br.CCCCOC1=CC(CBr)=CC(N)=C1CC1=CC=CC=C1 VTHLYRYVJCGRBR-UHFFFAOYSA-N 0.000 description 2
- PZTBQOIGTBMLNH-UHFFFAOYSA-N 2-benzyl-5-[(benzylamino)methyl]-3-butoxybenzenesulfonamide Chemical compound C=1C(S(N)(=O)=O)=C(CC=2C=CC=CC=2)C(OCCCC)=CC=1CNCC1=CC=CC=C1 PZTBQOIGTBMLNH-UHFFFAOYSA-N 0.000 description 2
- HVFBFJFZOCDTEN-UHFFFAOYSA-N 3-(butylamino)-5-cyano-2-phenoxybenzenesulfonamide Chemical compound CCCCNC1=CC(C#N)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 HVFBFJFZOCDTEN-UHFFFAOYSA-N 0.000 description 2
- LJCQTEGDYCSIOJ-UHFFFAOYSA-N 3-amino-5-(hydroxymethyl)-2-phenoxybenzenesulfonamide Chemical compound NC1=CC(CO)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 LJCQTEGDYCSIOJ-UHFFFAOYSA-N 0.000 description 2
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 2
- FMWFGTCTSJNEDX-UHFFFAOYSA-N 3-formylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C=O)=C1 FMWFGTCTSJNEDX-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 229940124591 thiazide-type diuretic Drugs 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DBODNPMIIRVQGW-UHFFFAOYSA-N trihydrate;dihydrochloride Chemical compound O.O.O.Cl.Cl DBODNPMIIRVQGW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2877375 | 1975-07-08 | ||
| GB2877575 | 1975-07-08 | ||
| GB2877475 | 1975-07-08 | ||
| GB28770/75A GB1523631A (en) | 1975-07-08 | 1975-07-08 | Sulphonamide derivatives |
| GB2877275 | 1975-07-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2630637A1 DE2630637A1 (de) | 1977-01-27 |
| DE2630637C2 true DE2630637C2 (de) | 1986-09-25 |
Family
ID=27516295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2630637A Expired DE2630637C2 (de) | 1975-07-08 | 1976-07-07 | Sulfamylbenzylaminderivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4082851A (Direct) |
| AT (1) | AT345783B (Direct) |
| AU (1) | AU503344B2 (Direct) |
| BE (1) | BE843828A (Direct) |
| CA (1) | CA1077953A (Direct) |
| DE (1) | DE2630637C2 (Direct) |
| DK (1) | DK302776A (Direct) |
| FI (1) | FI761987A7 (Direct) |
| FR (1) | FR2316929A1 (Direct) |
| GB (1) | GB1523631A (Direct) |
| GR (1) | GR60429B (Direct) |
| IE (1) | IE43009B1 (Direct) |
| IT (1) | IT1063145B (Direct) |
| LU (1) | LU75322A1 (Direct) |
| NL (1) | NL7607505A (Direct) |
| NZ (1) | NZ181168A (Direct) |
| PT (1) | PT65317B (Direct) |
| SE (1) | SE7607786L (Direct) |
| SU (1) | SU644374A3 (Direct) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4247550A (en) * | 1975-07-08 | 1981-01-27 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Compositions and methods for the treatment of hypertension or oedemas |
| CH628622A5 (de) * | 1976-12-24 | 1982-03-15 | Ciba Geigy Ag | Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren. |
| GB1600840A (en) * | 1978-05-30 | 1981-10-21 | Wellcome Found | Diphenylether derivatives useful as flukicidal agents |
| DE3041812A1 (de) * | 1980-11-06 | 1982-06-16 | Hoechst Ag, 6000 Frankfurt | Basisch substituierte 5-phenyltetrazole, verfahren zu ihrer herstellung und ihre verwendung als heilmittel |
| DE3208189A1 (de) * | 1982-03-06 | 1983-09-08 | Hoechst Ag, 6230 Frankfurt | 2-aminomethyl-6-sulfamoylphenolderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| MXPA01009733A (es) * | 1999-03-31 | 2002-11-04 | Basf Ag | Diamidas del acido piridin-2,3-dicarboxilico. |
| TWI449692B (zh) | 2005-05-13 | 2014-08-21 | Otsuka Pharma Co Ltd | 吡咯烷化合物（三） |
| SK542007A3 (sk) * | 2007-04-20 | 2008-11-06 | Unimed Pharma, Spol. S R. O. | Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2871233A (en) * | 1954-06-16 | 1959-01-27 | Basf Ag | Cobalt containing azo dyestuffs |
| US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
| US3565952A (en) * | 1968-09-06 | 1971-02-23 | Beiersdorf Ag | 4 - chloro - 3 - nitro - 5 - sulfamyl salicylic acid - (2',6' - dimethyl) - anilide and its salts |
| GB1249490A (en) * | 1968-12-24 | 1971-10-13 | Leo Pharm Prod Ltd | New sulphamyl-benzoic acid derivatives |
| US3806542A (en) * | 1969-06-10 | 1974-04-23 | Ciba Geigy Corp | 5-arylsulfamyl-anthranilic acids |
| US3706790A (en) * | 1970-02-27 | 1972-12-19 | Merck & Co Inc | (mono-and di-substituted sulfamoyl) benzoic acids |
| US3816482A (en) * | 1970-06-18 | 1974-06-11 | Leo Pharm Prod Ltd | Sulfamylbenzoic acids |
| US3860647A (en) * | 1973-08-20 | 1975-01-14 | Smithkline Corp | {60 -Aminomethyl-4-hydroxy-3-sulfamyl-benzyl alcohols and 4-hydroxy-3-sulfamyl phenethylamines |
| GB1434405A (en) * | 1973-09-06 | 1976-05-05 | Leo Pharm Prod Ltd | Phenyl-benzoic acid derivatives |
-
1975
- 1975-07-08 GB GB28770/75A patent/GB1523631A/en not_active Expired
-
1976
- 1976-06-14 IE IE1285/76A patent/IE43009B1/en unknown
- 1976-06-15 NZ NZ181168A patent/NZ181168A/xx unknown
- 1976-06-16 US US05/696,547 patent/US4082851A/en not_active Expired - Lifetime
- 1976-06-25 GR GR51105A patent/GR60429B/el unknown
- 1976-06-29 AT AT473076A patent/AT345783B/de not_active IP Right Cessation
- 1976-07-02 SU SU762377347A patent/SU644374A3/ru active
- 1976-07-02 PT PT65317A patent/PT65317B/pt unknown
- 1976-07-05 CA CA256,326A patent/CA1077953A/en not_active Expired
- 1976-07-05 DK DK302776A patent/DK302776A/da not_active Application Discontinuation
- 1976-07-06 BE BE168670A patent/BE843828A/xx unknown
- 1976-07-07 SE SE7607786A patent/SE7607786L/xx unknown
- 1976-07-07 LU LU75322A patent/LU75322A1/xx unknown
- 1976-07-07 FR FR7620790A patent/FR2316929A1/fr active Granted
- 1976-07-07 IT IT7668697A patent/IT1063145B/it active
- 1976-07-07 NL NL7607505A patent/NL7607505A/xx not_active Application Discontinuation
- 1976-07-07 FI FI761987A patent/FI761987A7/fi not_active Application Discontinuation
- 1976-07-07 AU AU15677/76A patent/AU503344B2/en not_active Expired
- 1976-07-07 DE DE2630637A patent/DE2630637C2/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Der am 15.05.85 eingegangene Versuchsbericht ist zur Einsicht für jedermann bereitzuhalten |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2316929A1 (fr) | 1977-02-04 |
| FI761987A7 (Direct) | 1977-01-09 |
| AU503344B2 (en) | 1979-08-30 |
| NL7607505A (nl) | 1977-01-11 |
| IE43009B1 (en) | 1980-12-03 |
| ATA473076A (de) | 1978-02-15 |
| FR2316929B1 (Direct) | 1979-09-21 |
| AT345783B (de) | 1978-10-10 |
| NZ181168A (en) | 1978-09-25 |
| DE2630637A1 (de) | 1977-01-27 |
| LU75322A1 (Direct) | 1977-04-01 |
| IE43009L (en) | 1977-01-08 |
| GR60429B (en) | 1978-05-26 |
| SE7607786L (sv) | 1977-01-09 |
| CA1077953A (en) | 1980-05-20 |
| GB1523631A (en) | 1978-09-06 |
| PT65317A (en) | 1976-08-01 |
| US4082851A (en) | 1978-04-04 |
| SU644374A3 (ru) | 1979-01-25 |
| AU1567776A (en) | 1978-01-12 |
| IT1063145B (it) | 1985-02-11 |
| PT65317B (en) | 1978-01-05 |
| DK302776A (da) | 1977-01-09 |
| BE843828A (fr) | 1977-01-06 |
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Legal Events
| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |