CH494230A - Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten - Google Patents

Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten

Info

Publication number: CH494230A
Authority: CH; Switzerland
Prior art keywords: prepared; sulfonamido; phenoxyacetic acid; dimethylamide; sep
Prior art date: 1966-04-27

Application number

CH599167A

Other languages

German (de)

English (en)

Inventor

Klaus Dr Gutsche

Hans Dr Priewe

Alois Dr Harwart

Original Assignee

Schering Ag

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.)

1966-04-27

Filing date

1967-04-27

Publication date

1970-07-31

1967-04-27 Application filed by Schering Ag filed Critical Schering Ag

1967-04-27 Priority to CH1691069A priority Critical patent/CH490390A/de

1967-04-27 Priority to CH1690969A priority patent/CH494232A/de

1967-04-27 Priority to CH1690869A priority patent/CH494231A/de

1970-07-31 Publication of CH494230A publication Critical patent/CH494230A/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 9
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
-1 aliphatic mono- Chemical class 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 30
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 9
229960003424 phenylacetic acid Drugs 0.000 claims description 6
239000003279 phenylacetic acid Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000002357 guanidines Chemical class 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
IIILLPUTZFBNTB-UHFFFAOYSA-N 2-(4-sulfamoylphenoxy)acetic acid Chemical compound NS(=O)(=O)C1=CC=C(OCC(O)=O)C=C1 IIILLPUTZFBNTB-UHFFFAOYSA-N 0.000 claims 15
239000008280 blood Substances 0.000 abstract description 7
210000004369 blood Anatomy 0.000 abstract description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
239000003826 tablet Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
229940124530 sulfonamide Drugs 0.000 description 3
150000003456 sulfonamides Chemical class 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
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 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 1
229960004257 sulfaguanidine Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH599167A 1966-04-27 1967-04-27 Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten CH494230A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH1691069A CH490390A (de)	1966-04-27	1967-04-27	Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten
CH1690969A CH494232A (de)	1967-04-27	1967-04-27	Verfahren zur Herstellung von 2-Sulfonamidopyrimidinderivaten
CH1690869A CH494231A (de)	1967-04-27	1967-04-27	Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DESC038898		1966-04-27

Publications (1)

Publication Number	Publication Date
CH494230A true CH494230A (de)	1970-07-31

Family

ID=7434907

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH599167A CH494230A (de)	1966-04-27	1967-04-27	Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten

Country Status (6)

Country	Link
BE (1)	BE697661A (da)
CH (1)	CH494230A (da)
DE (1)	DE1620461A1 (da)
DK (1)	DK116876B (da)
GB (1)	GB1188818A (da)
NL (1)	NL6705874A (da)

1966
- 1966-04-27 DE DE19661620461 patent/DE1620461A1/de active Pending
1967
- 1967-04-18 DK DK209167A patent/DK116876B/da unknown
- 1967-04-25 GB GB1892067A patent/GB1188818A/en not_active Expired
- 1967-04-26 NL NL6705874A patent/NL6705874A/xx unknown
- 1967-04-27 CH CH599167A patent/CH494230A/de not_active IP Right Cessation
- 1967-04-27 BE BE697661D patent/BE697661A/xx unknown

Also Published As

Publication number	Publication date
NL6705874A (da)	1967-10-30
GB1188818A (en)	1970-04-22
BE697661A (da)	1967-10-27
DK116876B (da)	1970-02-23
DE1620461A1 (de)	1970-04-09

Legal Events

Date	Code	Title	Description
1973-11-30	PL	Patent ceased

Publication	Publication Date	Title
DE2120495A1 (de)	1971-12-02	Neue Trialkoxychinazolin-Verbindungen und Verfahren zu ihrer Herstellung
CH626873A5 (da)	1981-12-15
DE2451161A1 (de)	1975-05-07	Stabile prostaglandin-e-gruppen enthaltende arzneimittelzubereitung sowie verfahren zu deren herstellung
CH494230A (de)	1970-07-31	Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten
DE3144689A1 (de)	1982-07-22	Antivirusmittel
DE2525249C2 (de)	1984-04-26	N,N'-(m-Phenylen)-dioxamsäuren und deren Derivate, Verfahren zur Herstellung derselben und dieselben enthaltende pharmazeutische Präparate
CH512450A (de)	1971-09-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE2029510C3 (de)	1980-06-19	Dibenzofuranderivate und deren pharmazeutisch verträgliche Säureadditionssalze sowie Verfahren zu deren Herstellung und Arzneimittel mit einem Gehalt dieser Verbindungen
DE1620177C3 (de)	1975-10-02	N-(2-Hydroxyäthyl)-piperazinocarboxymethyl-tetracyclin, dessen pharmakologisch verwendbaren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2236876B2 (de)	1980-06-04	N-Substituierte Aminocarbonsäuren und diese Verbindungen enthaltende Arzneimittel
CH490390A (de)	1970-05-15	Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten
CH494231A (de)	1970-07-31	Verfahren zur Herstellung von 2-Sulfonamidopyrimidin-derivaten
AT270660B (de)	1969-05-12	Verfahren zur Herstellung von neuen 2-Sulfonamidopyrimidinderivaten und deren Salzen
AT269884B (de)	1969-04-10	Verfahren zur Herstellung von neuen 2-Sulfonamidopyrimidinderivaten und deren Salzen
AT258925B (de)	1967-12-27	Verfahren zur Herstellung von neuen Pyrimidinderivaten
AT258301B (de)	1967-11-27	Verfahren zur Herstellung von neuen 2-Sulfonamido-pyrimidinderivaten und von deren Salzen
AT270661B (de)	1969-05-12	Verfahren zur Herstellung von neuen 2-Sulfonamidopyrimidinderivaten und deren Salzen
AT270662B (de)	1969-05-12	Verfahren zur Herstellung von neuen 2-Sulfonamidopyrimidinderivaten und deren Salzen
AT373584B (de)	1984-02-10	Verfahren zur herstellung neuer 2-pyridylaminobenzoesaeuren und ihre salze
DE1220421B (de)	1966-07-07	Verfahren zur Herstellung von 2-Pyridinaldehyd-guanylhydrazonen
DE2408522A1 (de)	1975-09-04	Aminderivate der azidophenole und verfahren zu ihrer herstellung
AT240861B (de)	1965-06-25	Verfahren zur Herstellung neuer Sulfonamide
DE1910560A1 (de)	1969-10-09	Neue Adamantanderivate
AT239236B (de)	1965-03-25	Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen
DE1961927C (de)	1972-11-16	1 ^-DiphenyM-n-butyl-S.S-dioxoparazolidin-Natrium-Monoglycerat, ein Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel