AT325608B - Verfahren zur herstellung neuer heterocyclischer verbindungen und ihren säureadditionssalze - Google Patents

Verfahren zur herstellung neuer heterocyclischer verbindungen und ihren säureadditionssalze

Info

Publication number: AT325608B
Authority: AT; Austria
Prior art keywords: general formula; group; methyl; heterocyclic compounds; compounds
Prior art date: 1969-02-20

Application number

AT983971A

Other languages

German (de)

English (en)

Original Assignee

Wander Ag Dr A

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.)

1969-02-20

Filing date

1970-02-18

Publication date

1975-10-27

1969-02-20 Priority claimed from CH257569A external-priority patent/CH511815A/de

1970-02-18 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1975-10-27 Application granted granted Critical

1975-10-27 Publication of AT325608B publication Critical patent/AT325608B/de

Links

239000002253 acid Substances 0.000 title claims description 7
150000003839 salts Chemical class 0.000 title claims description 7
150000002391 heterocyclic compounds Chemical class 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 5
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000004985 diamines Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
YMPKGRGRMBFGHC-UHFFFAOYSA-N methyl n'-[2-(2,6-dichlorophenyl)acetyl]carbamimidothioate Chemical compound CSC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl YMPKGRGRMBFGHC-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
PPHRVEGSUCPURL-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-(4,5-dihydro-1H-imidazol-2-yl)acetamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N=C1NCCN1 PPHRVEGSUCPURL-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
WZMHFVBIQHZZNN-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-(1,4,5,6-tetrahydropyrimidin-2-yl)acetamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N=C1NCCCN1 WZMHFVBIQHZZNN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
-1 2- [2- (2,6-dichlorophenyl) acetylimino] hexahydropyrimidine hydrochloride Chemical compound 0.000 description 1
VFRDBQGBQYINBH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=C(Cl)C=CC=C1Cl VFRDBQGBQYINBH-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
208000007530 Essential hypertension Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
241001465754 Metazoa Species 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
KRYWEAYKLGCRRH-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]azanium;chloride Chemical compound Cl.CSC(N)=N KRYWEAYKLGCRRH-UHFFFAOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001631 hypertensive effect Effects 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
239000008101 lactose Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

AT983971A 1969-02-20 1970-02-18 Verfahren zur herstellung neuer heterocyclischer verbindungen und ihren säureadditionssalze AT325608B (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH257569A CH511815A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen
CH1657569		1969-11-07

Publications (1)

Publication Number	Publication Date
AT325608B true AT325608B (de)	1975-10-27

Family

ID=25690815

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT983971A AT325608B (de)	1969-02-20	1970-02-18	Verfahren zur herstellung neuer heterocyclischer verbindungen und ihren säureadditionssalze

Country Status (2)

Country	Link
AT (1)	AT325608B (cs)
CS (1)	CS158266B2 (cs)

1970
- 1970-02-18 CS CS569272A patent/CS158266B2/cs unknown
- 1970-02-18 AT AT983971A patent/AT325608B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CS158266B2 (cs)	1974-10-15

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Legal Events

Date	Code	Title	Description
1977-10-15	ELJ	Ceased due to non-payment of the annual fee