DE2723635A1 - Subst.-2-aminomethylphenyl-hydrogensulfate - Google Patents

Subst.-2-aminomethylphenyl-hydrogensulfate

Info

Publication number: DE2723635A1
Authority: DE; Germany
Prior art keywords: carbon atoms; hydrogen; alkyl; chlorine; pharmaceutically acceptable
Prior art date: 1976-05-26
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.): Ceased

Application number

DE19772723635

Other languages

German (de)

English (en)

Inventor

Jun Edward Jethro Cragoe

Robert Lawrence Smith

Gerald Edward Stokker

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.)

Merck and Co Inc

Original Assignee

Merck and Co Inc

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.)

1976-05-26

Filing date

1977-05-25

Publication date

1977-12-08

1977-05-25 Application filed by Merck and Co Inc filed Critical Merck and Co Inc

1977-12-08 Publication of DE2723635A1 publication Critical patent/DE2723635A1/de

Status Ceased legal-status Critical Current

Links

229910052739 hydrogen Inorganic materials 0.000 title claims description 24
239000001257 hydrogen Substances 0.000 title claims description 23
-1 2-AMINOMETHYLPHENYL HYDROGEN SULPHATES Chemical class 0.000 title claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 31
239000000460 chlorine Substances 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 12
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000011630 iodine Chemical group 0.000 claims description 10
229910052740 iodine Inorganic materials 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
IRDCWFAOPAYRKP-UHFFFAOYSA-N [2-(aminomethyl)-4-tert-butyl-6-iodophenyl] hydrogen sulfate Chemical compound CC(C)(C)C1=CC(I)=C(OS(O)(=O)=O)C(CN)=C1 IRDCWFAOPAYRKP-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 3
206010030113 Oedema Diseases 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
239000000825 pharmaceutical preparation Substances 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 2
239000012429 reaction media Substances 0.000 claims 2
TXENPQZYQPWRAV-UHFFFAOYSA-N (2-ethylphenyl) hydrogen sulfate Chemical compound CCC1=CC=CC=C1OS(O)(=O)=O TXENPQZYQPWRAV-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
VGAFEISLRCBKJM-UHFFFAOYSA-N [2-(aminomethyl)phenyl] hydrogen sulfate Chemical class NCC1=CC=CC=C1OS(O)(=O)=O VGAFEISLRCBKJM-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000002934 diuretic Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
KPRZOPQOBJRYSW-UHFFFAOYSA-N 2-(aminomethyl)phenol Chemical class NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000002552 dosage form 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
CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
SSEAPVMQZPKNQZ-UHFFFAOYSA-N 2-(aminomethyl)-4-tert-butyl-6-iodophenol Chemical compound CC(C)(C)C1=CC(I)=C(O)C(CN)=C1 SSEAPVMQZPKNQZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
239000008101 lactose Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000000894 saliuretic effect Effects 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
DGPRKNZJZXMVRU-UHFFFAOYSA-N (2-iodophenyl) hydrogen sulfate Chemical compound S(=O)(=O)(O)OC1=C(C=CC=C1)I DGPRKNZJZXMVRU-UHFFFAOYSA-N 0.000 description 1
UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
HJCYVBBGVRHXKR-UHFFFAOYSA-N 2-(aminomethyl)-4-tert-butyl-6-iodophenol;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC(I)=C(O)C(CN)=C1 HJCYVBBGVRHXKR-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
OMGLZZKQBOFWRG-UHFFFAOYSA-N Cl.CC(C)(C)C1=CC(I)=C(O)C(CCN)=C1 Chemical compound Cl.CC(C)(C)C1=CC(I)=C(O)C(CCN)=C1 OMGLZZKQBOFWRG-UHFFFAOYSA-N 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
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000010835 comparative analysis Methods 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229940045996 isethionic acid Drugs 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
UFWWAKOWSBGGCP-UHFFFAOYSA-N pyridine;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=NC=C1 UFWWAKOWSBGGCP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940124597 therapeutic agent Drugs 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/14—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and unsaturated
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Detergent Compositions (AREA)

DE19772723635 1976-05-26 1977-05-25 Subst.-2-aminomethylphenyl-hydrogensulfate Ceased DE2723635A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US69032276A	1976-05-26	1976-05-26

Publications (1)

Publication Number	Publication Date
DE2723635A1 true DE2723635A1 (de)	1977-12-08

Family

ID=24772019

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19772723635 Ceased DE2723635A1 (de)	1976-05-26	1977-05-25	Subst.-2-aminomethylphenyl-hydrogensulfate

Country Status (12)

Country	Link
JP (1)	JPS52144648A (nl)
AU (1)	AU2520777A (nl)
BE (1)	BE855023A (nl)
DE (1)	DE2723635A1 (nl)
DK (1)	DK206777A (nl)
ES (1)	ES459100A1 (nl)
FR (1)	FR2352795A1 (nl)
GB (1)	GB1543886A (nl)
HU (1)	HU173761B (nl)
NL (1)	NL7705089A (nl)
SE (1)	SE7705499L (nl)
ZA (1)	ZA773158B (nl)

1977
- 1977-05-09 NL NL7705089A patent/NL7705089A/nl not_active Application Discontinuation
- 1977-05-11 SE SE7705499A patent/SE7705499L/xx unknown
- 1977-05-11 DK DK206777A patent/DK206777A/da unknown
- 1977-05-17 AU AU25207/77A patent/AU2520777A/en not_active Expired
- 1977-05-23 GB GB21637/77A patent/GB1543886A/en not_active Expired
- 1977-05-24 ES ES459100A patent/ES459100A1/es not_active Expired
- 1977-05-25 DE DE19772723635 patent/DE2723635A1/de not_active Ceased
- 1977-05-25 ZA ZA00773158A patent/ZA773158B/xx unknown
- 1977-05-25 FR FR7715956A patent/FR2352795A1/fr active Granted
- 1977-05-25 BE BE177891A patent/BE855023A/xx unknown
- 1977-05-26 HU HU77ME2072A patent/HU173761B/hu unknown
- 1977-05-26 JP JP6056977A patent/JPS52144648A/ja active Granted

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Houben-Weyl: Methoden der organischen Chemie, 4. Aufl., Bd. IX, S. 506-508 *

Also Published As

Publication number	Publication date
GB1543886A (en)	1979-04-11
FR2352795A1 (fr)	1977-12-23
JPS6126537B2 (nl)	1986-06-20
ZA773158B (en)	1979-01-31
AU2520777A (en)	1978-11-23
SE7705499L (sv)	1977-11-27
JPS52144648A (en)	1977-12-02
ES459100A1 (es)	1978-11-01
DK206777A (da)	1977-11-27
HU173761B (hu)	1979-08-28
BE855023A (fr)	1977-11-25
FR2352795B1 (nl)	1979-03-23
NL7705089A (nl)	1977-11-29

Publication	Publication Date	Title
DE1815922C3 (de)	1979-04-26	5-Phenyltetrazol-Derivate
DE1470053A1 (de)	1969-06-26	5,6-disubstituierte (3-Aminopyrazinoyl)-guanidinverbindungen und Verfahren zu deren Herstellung
DE1518874C3 (de)	1975-03-13	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
DE1568349A1 (de)	1970-02-12	Neue Diphenylharnstoffe und Verfahren zu ihrer Herstellung
DE2723635A1 (de)	1977-12-08	Subst.-2-aminomethylphenyl-hydrogensulfate
DE1543564A1 (de)	1970-09-17	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
DE2726793A1 (de)	1977-12-22	2-imino-3-aminothiazolidine
DE1518816C3 (de)	1975-05-22	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE1165033B (de)	1964-03-12	Verfahren zur Herstellung von Sulfamylsaccharinverbindungen.
DE1443911A1 (de)	1969-04-30	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
EP0011603A1 (de)	1980-05-28	10-Cyan-5H-dibenz(b,f)azepin-5-carboxamid, Verfahren zu seiner Herstellung und pharmazeutische Präparate, welche diese Verbindung enthalten
CH633962A5 (en)	1983-01-14	Pharmaceutical preparations which contain pteridine compounds
DE2443539C3 (de)	1978-11-23	Ester der 5-n-Butyl-pyridin-carbonsäure- (2), Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
DE2155660C3 (de)	1979-06-21	4,7-Methano-isoindolinoderivate und Verfahren zu deren Herstellung
DE1443905B2 (de)	1978-07-13	N-[4-(ß- {a-Chlor- 4-chlorphenyl-acetamido} -äthyl)benzolsulfonyl] -N'-cycIohexylharnstoff, Verfahren zu seiner Herstellung und seine Verwendung
DE1126862B (de)	1962-04-05	Verfahren zur Herstellung von substituierten Benzol-m-disulfonamiden
AT339915B (de)	1977-11-10	Verfahren zur herstellung von neuen acylaminoathylbenzolsulfonylharnstoffen und von deren salzen
AT252940B (de)	1967-03-10	Verfahren zur Herstellung von neuen N-(ω-Guanidino-alkyl)-azaspiroalkanen
DE1620747B2 (nl)	1974-04-18
DE3220185A1 (de)	1982-12-23	4-amino-benzylamin-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als pharmazeutica
DE2002107A1 (de)	1970-07-30	Neue organische Verbindungen und Verfahren zu deren Herstellung
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