CA1056836A - Les 2-phenyliminoimidazolidines substituees en 2,6, leurs sels d'addition, produits pharmaceutiques qui en contiennent et procede pour leur production - Google Patents

Les 2-phenyliminoimidazolidines substituees en 2,6, leurs sels d'addition, produits pharmaceutiques qui en contiennent et procede pour leur production

Info

Publication number: CA1056836A
Authority: CA; Canada
Prior art keywords: formula; process according; chloro; methylphenyl; acid addition
Prior art date: 1974-10-01
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

Application number

CA236,670A

Other languages

English (en)

Inventor

Wolfgang Hoefke

Werner Kummer

Herbert Koppe

Helmut Stahle

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim GmbH

Original Assignee

Boehringer Ingelheim GmbH

Priority date (The priority date 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 date listed.)

1974-10-01

Filing date

1975-09-30

Publication date

1979-06-19

1975-09-30 Application filed by Boehringer Ingelheim GmbH filed Critical Boehringer Ingelheim GmbH

1979-06-19 Application granted granted Critical

1979-06-19 Publication of CA1056836A publication Critical patent/CA1056836A/fr

Status Expired legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 49
239000002253 acid Substances 0.000 title claims abstract description 45
238000000034 method Methods 0.000 title claims abstract description 39
230000008569 process Effects 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title abstract description 9
JCOPITWIWLFFPC-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical class N1CCN=C1NC1=CC=CC=C1 JCOPITWIWLFFPC-UHFFFAOYSA-N 0.000 title description 2
239000003814 drug Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 59
238000002360 preparation method Methods 0.000 claims abstract description 10
-1 2-ethyl-6-methylphenyl Chemical group 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
RAGMNJMOWFXIOX-UHFFFAOYSA-N n-[2-chloro-6-(trifluoromethyl)phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(Cl)=C1NC1=NCCN1 RAGMNJMOWFXIOX-UHFFFAOYSA-N 0.000 claims description 3
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
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 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 6
229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
UJVKFRXRRKMMQJ-UHFFFAOYSA-N n-[2,6-bis(trifluoromethyl)phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1N=C1NCCN1 UJVKFRXRRKMMQJ-UHFFFAOYSA-N 0.000 claims 2
VJLADBUFZUFOCT-UHFFFAOYSA-N n-[2-fluoro-6-(trifluoromethyl)phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound FC1=CC=CC(C(F)(F)F)=C1NC1=NCCN1 VJLADBUFZUFOCT-UHFFFAOYSA-N 0.000 claims 2
230000036772 blood pressure Effects 0.000 abstract description 4
239000008194 pharmaceutical composition Substances 0.000 abstract description 3
206010020852 Hypertonia Diseases 0.000 abstract description 2
230000003247 decreasing effect Effects 0.000 abstract description 2
235000002639 sodium chloride Nutrition 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 17
239000004480 active ingredient Substances 0.000 description 15
229940012017 ethylenediamine Drugs 0.000 description 15
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
125000004429 atom Chemical group 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
229960000443 hydrochloric acid Drugs 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000005711 Benzoic acid Substances 0.000 description 4
RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
238000001035 drying Methods 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
239000000546 pharmaceutical excipient Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000012730 sustained-release form Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
239000008346 aqueous phase Substances 0.000 description 3
235000010233 benzoic acid Nutrition 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
238000001816 cooling Methods 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
238000005947 deacylation reaction Methods 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
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UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
LDSSGKZZKNPFDT-UHFFFAOYSA-N FC(C1=C(C(=CC=C1)C(F)(F)F)[Li])(F)F Chemical compound FC(C1=C(C(=CC=C1)C(F)(F)F)[Li])(F)F LDSSGKZZKNPFDT-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
238000000297 Sandmeyer reaction Methods 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
241000543375 Sideroxylon Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
239000003613 bile acid Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940096529 carboxypolymethylene Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
CJCFPGYYZOBPHN-UHFFFAOYSA-N n-phenylimidazolidin-2-amine Chemical class N1CCNC1NC1=CC=CC=C1 CJCFPGYYZOBPHN-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000005338 nitrobenzoic acids Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
238000009938 salting Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA236,670A 1974-10-01 1975-09-30 Les 2-phenyliminoimidazolidines substituees en 2,6, leurs sels d'addition, produits pharmaceutiques qui en contiennent et procede pour leur production Expired CA1056836A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2446758A DE2446758C3 (de)	1974-10-01	1974-10-01	2-(2-Fluor-6-trifluormethylphenylimino)-imidazolidin, dessen Säureadditionssalze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung der Hypertonie

Publications (1)

Publication Number	Publication Date
CA1056836A true CA1056836A (fr)	1979-06-19

Family

ID=5927202

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,670A Expired CA1056836A (fr)	1974-10-01	1975-09-30	Les 2-phenyliminoimidazolidines substituees en 2,6, leurs sels d'addition, produits pharmaceutiques qui en contiennent et procede pour leur production

Country Status (27)

Country	Link
JP (1)	JPS6018653B2 (fr)
AT (1)	AT344159B (fr)
BE (1)	BE834051A (fr)
BG (2)	BG25221A3 (fr)
CA (1)	CA1056836A (fr)
CH (5)	CH620682A5 (fr)
CS (1)	CS193524B2 (fr)
DD (1)	DD123602A5 (fr)
DE (1)	DE2446758C3 (fr)
DK (1)	DK441875A (fr)
ES (4)	ES441385A1 (fr)
FI (1)	FI61883C (fr)
FR (1)	FR2286649A1 (fr)
GB (1)	GB1515019A (fr)
HU (1)	HU178469B (fr)
IE (1)	IE42130B1 (fr)
IL (1)	IL48214A (fr)
LU (1)	LU73472A1 (fr)
NL (1)	NL7511490A (fr)
NO (1)	NO143459C (fr)
NZ (1)	NZ178810A (fr)
PH (1)	PH13653A (fr)
PL (2)	PL98984B1 (fr)
SE (1)	SE418497B (fr)
SU (1)	SU575026A3 (fr)
YU (1)	YU230281A (fr)
ZA (1)	ZA756185B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2630060C2 (de) *	1976-07-03	1984-04-19	C.H. Boehringer Sohn, 6507 Ingelheim	2-(2-Brom-6-fluor-phenylimino)-imidazolidin, dessen Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung
DE2806811A1 (de) *	1978-02-17	1979-08-23	Boehringer Sohn Ingelheim	Neue substituierte 2-phenylimino- imidazolidine, deren saeureadditionssalze, diese enthaltene arzneimittel und verfahren zur herstellung derselben
DE2806775A1 (de) *	1978-02-17	1979-08-30	Boehringer Sohn Ingelheim	Neue substituierte 2-phenylimino- imidazolidine deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
CA1138451A (fr) *	1979-04-03	1982-12-28	Ikuo Ueda	Derives de la 2-imidazoline, procede de preparation et composes pharmaceutiques les contenant
HU192986B (en) *	1984-05-23	1987-08-28	Egyt Gyogyszervegyeszeti Gyar	Process for production of imidasodiline derivatives
BRPI0707308A2 (pt) *	2006-01-27	2011-05-03	Hoffmann La Roche	uso de 2-imidazóis para o tratamento de distúrbios do snc
RU2473545C2 (ru)	2007-02-02	2013-01-27	Ф.Хоффманн-Ля Рош Аг	Новые 2-аминооксазолины в качестве лигандов taar1 для заболеваний цнс
KR101222412B1 (ko)	2007-02-15	2013-01-15	에프. 호프만-라 로슈 아게	Ｔａａｒ1 리간드로서의 2-아미노옥사졸린
US8242153B2 (en)	2008-07-24	2012-08-14	Hoffmann-La Roche Inc.	4,5-dihydro-oxazol-2YL derivatives
US8354441B2 (en)	2009-11-11	2013-01-15	Hoffmann-La Roche Inc.	Oxazoline derivatives
US9452980B2 (en)	2009-12-22	2016-09-27	Hoffmann-La Roche Inc.	Substituted benzamides
SG11201807516UA (en)	2016-03-17	2018-09-27	Hoffmann La Roche	5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3236857A (en) *	1961-10-09	1966-02-22	Boehringer Sohn Ingelheim	2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products
DE1670807A1 (de) *	1967-02-17	1971-03-11	Bayer Ag	Verfahren zur Herstellung von cyclischen Guanidinen
DE1670918A1 (de) *	1967-09-07	1971-04-08	Bayer Ag	Verfahren zur Herstellung von 2-Aryl-amino-substituierten stickstoffhaltigen Heterocyclen
BE787683A (fr) *	1971-08-20	1973-02-19	Boehringer Sohn Ingelheim	2-phenylimino-imidazolidines, leurs sels d'addition avec des acides et procedes pour les fabriquer

1974
- 1974-10-01 DE DE2446758A patent/DE2446758C3/de not_active Expired
1975
- 1975-09-22 AT AT722875A patent/AT344159B/de not_active IP Right Cessation
- 1975-09-23 SU SU7502174605A patent/SU575026A3/ru active
- 1975-09-26 PH PH17613A patent/PH13653A/en unknown
- 1975-09-29 DD DD188613A patent/DD123602A5/xx unknown
- 1975-09-29 CS CS756573A patent/CS193524B2/cs unknown
- 1975-09-29 BG BG032014A patent/BG25221A3/xx unknown
- 1975-09-29 BG BG031110A patent/BG25220A3/xx unknown
- 1975-09-29 LU LU73472A patent/LU73472A1/xx unknown
- 1975-09-30 NO NO753314A patent/NO143459C/no unknown
- 1975-09-30 CH CH1267875A patent/CH620682A5/de not_active IP Right Cessation
- 1975-09-30 CA CA236,670A patent/CA1056836A/fr not_active Expired
- 1975-09-30 ZA ZA756185A patent/ZA756185B/xx unknown
- 1975-09-30 HU HU75BO1573A patent/HU178469B/hu unknown
- 1975-09-30 DK DK441875A patent/DK441875A/da not_active Application Discontinuation
- 1975-09-30 IL IL48214A patent/IL48214A/xx unknown
- 1975-09-30 PL PL1975197816A patent/PL98984B1/pl unknown
- 1975-09-30 ES ES441385A patent/ES441385A1/es not_active Expired
- 1975-09-30 JP JP50118196A patent/JPS6018653B2/ja not_active Expired
- 1975-09-30 GB GB40012/75A patent/GB1515019A/en not_active Expired
- 1975-09-30 FI FI752728A patent/FI61883C/fi not_active IP Right Cessation
- 1975-09-30 BE BE160578A patent/BE834051A/fr not_active IP Right Cessation
- 1975-09-30 PL PL1975183670A patent/PL97003B1/pl unknown
- 1975-09-30 NZ NZ178810A patent/NZ178810A/xx unknown
- 1975-09-30 NL NL7511490A patent/NL7511490A/xx not_active Application Discontinuation
- 1975-10-01 IE IE2150/75A patent/IE42130B1/en unknown
- 1975-10-01 FR FR7530117A patent/FR2286649A1/fr active Granted
- 1975-10-01 SE SE7511028A patent/SE418497B/xx not_active IP Right Cessation
1976
- 1976-02-04 ES ES444898A patent/ES444898A1/es not_active Expired
- 1976-02-04 ES ES444901A patent/ES444901A1/es not_active Expired
- 1976-02-04 ES ES444900A patent/ES444900A1/es not_active Expired
1980
- 1980-07-01 CH CH506480A patent/CH626352A5/de not_active IP Right Cessation
- 1980-07-01 CH CH506280A patent/CH627452A5/de not_active IP Right Cessation
- 1980-07-01 CH CH506380A patent/CH627453A5/de not_active IP Right Cessation
- 1980-07-01 CH CH506580A patent/CH627454A5/de not_active IP Right Cessation
1981
- 1981-09-24 YU YU02302/81A patent/YU230281A/xx unknown

Also Published As

Publication number	Publication date
FR2286649A1 (fr)	1976-04-30
FR2286649B1 (fr)	1979-09-14
YU230281A (en)	1982-02-28
ATA722875A (de)	1977-11-15
ES441385A1 (es)	1977-08-01
SE418497B (sv)	1981-06-09
NL7511490A (nl)	1976-04-05
NZ178810A (en)	1978-04-03
ES444901A1 (es)	1977-04-16
DE2446758A1 (de)	1976-04-22
JPS5159863A (en)	1976-05-25
IL48214A0 (en)	1975-11-25
PL97003B1 (pl)	1978-01-31
CH620682A5 (en)	1980-12-15
IE42130B1 (en)	1980-06-04
LU73472A1 (fr)	1977-05-16
NO753314L (fr)	1976-04-02
CH627453A5 (en)	1982-01-15
DD123602A5 (fr)	1977-01-05
FI752728A (fr)	1976-04-02
CS193524B2 (en)	1979-10-31
IL48214A (en)	1979-10-31
NO143459C (no)	1981-02-18
HU178469B (en)	1982-05-28
NO143459B (no)	1980-11-10
AU8529875A (en)	1977-04-07
FI61883B (fi)	1982-06-30
BE834051A (fr)	1976-03-30
CH626352A5 (en)	1981-11-13
AT344159B (de)	1978-07-10
BG25220A3 (en)	1978-08-10
PH13653A (en)	1980-08-21
BG25221A3 (en)	1978-08-10
DE2446758C3 (de)	1979-01-04
IE42130L (en)	1976-04-01
ES444898A1 (es)	1977-05-16
DK441875A (da)	1976-04-02
JPS6018653B2 (ja)	1985-05-11
DE2446758B2 (de)	1978-05-18
FI61883C (fi)	1982-10-11
SE7511028L (sv)	1976-04-02
ES444900A1 (es)	1977-04-16
GB1515019A (en)	1978-06-21
CH627454A5 (en)	1982-01-15
SU575026A3 (ru)	1977-09-30
PL98984B1 (pl)	1978-06-30
CH627452A5 (en)	1982-01-15
ZA756185B (en)	1977-06-29

Publication	Publication Date	Title
US4125620A (en)	1978-11-14	2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof
EP0269378B1 (fr)	1991-01-23	Dérivé de la quinazolinone et procédés pour sa préparation
CA1056836A (fr)	1979-06-19	Les 2-phenyliminoimidazolidines substituees en 2,6, leurs sels d'addition, produits pharmaceutiques qui en contiennent et procede pour leur production
KR930002492B1 (ko)	1993-04-02	6-티오크산틴 유도체의 제조방법
HUT61984A (en)	1993-03-29	Process for producing condensed imidazole derivatives and pharmaceutical compositions comprising same
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
KR900008674B1 (ko)	1990-11-26	N-(피페리디닐-알킬)-카복스아미드의 제조방법
HU200597B (en)	1990-07-28	Process for producing sulfonylurea derivatives with antitumour effect
EA006400B1 (ru)	2005-12-29	Стабильная полиморфная модификация флибансерина, способ её промышленного получения и её применение для получения лекарственных средств
EP0070562B1 (fr)	1985-06-12	Dérivés d'ergoline, leur procédé de préparation et compositions pharmaceutiques les contenant
GB2088869A (en)	1982-06-16	8-arylalkyl-3-phenyl-3-nortropanols
US3850926A (en)	1974-11-26	2-(n-substituted-phenylamino)-imidazolines-(2)
CA1088550A (fr)	1980-10-28	2-bromo-6-fluoro-n-2-imidazolidinylidene-benzamine
IE48073B1 (en)	1984-09-19	Substituted 2-phenylimino-imidazolidines
JPS6040422B2 (ja)	1985-09-11	置換１‐アルキルチオフエニル―２，３，４，５―テトラヒドロ―１ｈ―３―ベンズアゼピン化合物
EP0229329B1 (fr)	1993-07-28	Dérivés de benzazépine
US3937717A (en)	1976-02-10	2-phenylamino-imidazolines-(2)
IL112364A (en)	1998-01-04	Pharmaceutical preparations containing 3-phenylsulfonyl-3,7-diazabicyclo [1.3.3] nonanan compounds for the treatment of heart rhythm disorders and certain new compounds and their preparation
EP0594883A1 (fr)	1994-05-04	Dérivés d'imidazo(1,2,c)quinazoline comme antihypertensives et antidysuriques
EP0394484B1 (fr)	1995-02-15	Derives de benzothiadiazepine
US4728649A (en)	1988-03-01	3-oxo-piperazin-1-yl-ergolines exhibiting antidopaminergic activity
US4210659A (en)	1980-07-01	Substituted 7-phenyl-2,3-dihydro-imidazo[1,2-α]imidazoles and salts thereof
EP0347880A2 (fr)	1989-12-27	Composés d'imidazo[2,1-b]benzothiazole et compositions anti-ulcère les contenant
HU192501B (en)	1987-06-29	Process for producing /2-methyl-propoxy/-methyl-n-phenyl-n-/phenyl-methyl/-1-pyrrolidin-ethanamine
US4263300A (en)	1981-04-21	Substituted 2-phenylamino-1,3-tetrahydro-2-pyrimidines and salts thereof