CH523231A - Verfahren zur Herstellung von Acylguanidinen - Google Patents

Verfahren zur Herstellung von Acylguanidinen

Info

Publication number: CH523231A
Authority: CH; Switzerland
Prior art keywords: formula; hydrogen; methyl; acid; compounds
Prior art date: 1969-02-20

Application number

CH416471A

Other languages

German (de)

English (en)

Inventor

Bernard Bream John

Wolfgang Dr Picard Claud

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

1969-02-20

Publication date

1972-05-31

1969-02-20 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1969-02-20 Priority to CH416471A priority Critical patent/CH523231A/de

1972-05-31 Publication of CH523231A publication Critical patent/CH523231A/de

Links

ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title abstract 4
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title abstract 2
229940030600 antihypertensive agent Drugs 0.000 title abstract 2
239000002220 antihypertensive agent Substances 0.000 title abstract 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
150000004985 diamines Chemical class 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 5
239000000460 chlorine Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
239000007858 starting material Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
-1 p-nitrobenzylthio group Chemical group 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
125000004659 aryl alkyl thio group Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000047 product Substances 0.000 description 3
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 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
150000004820 halides Chemical class 0.000 description 2
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 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
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 1
KVXFVZALHMVMMK-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-(N'-propan-2-ylcarbamimidoyl)acetamide Chemical compound CC(C)NC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl KVXFVZALHMVMMK-UHFFFAOYSA-N 0.000 description 1
DWKXVEAAWGYUPX-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-(N,N'-dimethylcarbamimidoyl)acetamide Chemical compound CNC(NC)=NC(=O)CC1=C(Cl)C=CC=C1Cl DWKXVEAAWGYUPX-UHFFFAOYSA-N 0.000 description 1
FKPBQQYWBAJQJC-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-[N'-(3-hydroxypropyl)carbamimidoyl]acetamide Chemical compound NC(NCCCO)=NC(=O)CC1=C(Cl)C=CC=C1Cl FKPBQQYWBAJQJC-UHFFFAOYSA-N 0.000 description 1
MTXRYLDKVRPTGG-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(n'-ethylcarbamimidoyl)acetamide Chemical compound CCN=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl MTXRYLDKVRPTGG-UHFFFAOYSA-N 0.000 description 1
COJLHPSZVYZSGJ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(n'-propylcarbamimidoyl)acetamide Chemical compound CCCN=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl COJLHPSZVYZSGJ-UHFFFAOYSA-N 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
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-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
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
241001465754 Metazoa Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 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
KRYWEAYKLGCRRH-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]azanium;chloride Chemical compound Cl.CSC(N)=N KRYWEAYKLGCRRH-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 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
235000011114 ammonium hydroxide Nutrition 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
150000003842 bromide salts Chemical class 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
150000001805 chlorine compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 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
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
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000000203 mixture Substances 0.000 description 1
OGTSEJZIUMTBRW-UHFFFAOYSA-N n-[amino(dimethylamino)methylidene]-2-(2,6-dichlorophenyl)acetamide Chemical compound CN(C)C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl OGTSEJZIUMTBRW-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
- 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
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
- 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/16—Nitrogen atoms not forming part of a nitro radical acylated on said nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D247/00—Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00
- C07D247/02—Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00 having the nitrogen atoms in positions 1 and 3

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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH416471A 1969-02-20 1969-02-20 Verfahren zur Herstellung von Acylguanidinen CH523231A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH416471A CH523231A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH416471A CH523231A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen
CH257569A CH511815A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen

Publications (1)

Publication Number	Publication Date
CH523231A true CH523231A (de)	1972-05-31

Family

ID=4236878

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH416471A CH523231A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen
CH416571A CH526550A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen
CH257569A CH511815A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH416571A CH526550A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen
CH257569A CH511815A (de)	1969-02-20	1969-02-20	Verfahren zur Herstellung von Acylguanidinen

Country Status (6)

Country	Link
AT (1)	AT309415B (cs)
BR (1)	BR7016868D0 (cs)
CH (3)	CH523231A (cs)
CS (1)	CS158265B2 (cs)
SU (2)	SU401047A3 (cs)
ZA (1)	ZA701134B (cs)

1969
- 1969-02-20 CH CH416471A patent/CH523231A/de not_active IP Right Cessation
- 1969-02-20 CH CH416571A patent/CH526550A/de not_active IP Right Cessation
- 1969-02-20 CH CH257569A patent/CH511815A/de not_active IP Right Cessation
1970
- 1970-02-18 CS CS569172*1A patent/CS158265B2/cs unknown
- 1970-02-18 SU SU1619810A patent/SU401047A3/ru active
- 1970-02-18 AT AT983871A patent/AT309415B/de not_active IP Right Cessation
- 1970-02-18 SU SU1620555A patent/SU457219A3/ru active
- 1970-02-19 BR BR216868/70A patent/BR7016868D0/pt unknown
- 1970-02-20 ZA ZA701134A patent/ZA701134B/xx unknown

Also Published As

Publication number	Publication date
AT309415B (de)	1973-08-27
CH511815A (de)	1971-08-31
CH526550A (de)	1972-08-15
CS158265B2 (cs)	1974-10-15
SU457219A3 (ru)	1975-01-15
SU401047A3 (cs)	1973-10-01
BR7016868D0 (pt)	1973-01-09
ZA701134B (en)	1971-09-29

Legal Events

Date	Code	Title	Description
1978-10-13	PL	Patent ceased

Publication	Publication Date	Title
DE2503815C2 (de)	1986-05-22	Indazol-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel
CH428747A (de)	1967-01-31	Verfahren zur Herstellung neuer Harnstoff- und Thioharnstoffderivate
DE1118789B (de)	1961-12-07	Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten
DE1620449B2 (de)	1973-07-26	Substituierte benzimidazole und verfahren zu ihrer herstellung
DE2006895A1 (de)	1970-09-10	Neue Phenacetylguanidine und Verfahren zu ihrer Herstellung
CH620898A5 (cs)	1980-12-31
DE2128941A1 (de)	1971-12-16	Neue Derivate des 2 Amino 5 Chlor Thiazols
DE1901497A1 (de)	1969-08-28	Neue heterocyclische Verbindungen und Verfahren zu ihrer Herstellung
CH523231A (de)	1972-05-31	Verfahren zur Herstellung von Acylguanidinen
CH638980A5 (de)	1983-10-31	Pharmazeutisches praeparat mit insbesondere diuretischer wirkung, enthaltend ein derivat des 2,4,7-triamino-6-phenylpteridins.
DE1470421A1 (de)	1969-06-26	Mehrbasische Verbindungen
DE2732029A1 (de)	1979-02-01	Neue amidino-benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE1670143C3 (cs)	1974-05-30
DE971002C (de)	1958-11-27	Verfahren zur Herstellung von Thioxanthonen
CH513848A (de)	1971-10-15	Verfahren zur Herstellung von Pyrrolinverbindungen
DE1241437B (de)	1967-06-01	Verfahren zur Herstellung von Biguanid-guanylhydrazonverbindungen
DE1468351C (de)	1971-07-01	Verfahren zur Herstellung von Hydro Chloriden von N Aryl und N Heteroarlyami dinen
DE1670162C3 (de)	1979-02-22	Verfahren zur Herstellung von 2-substituierten Phenylamino-13-diazacycloalkenen-(2) und dessen Säureadditionssalzen
AT273961B (de)	1969-09-10	Verfahren zur Herstellung von neuen 2-Benzylamino-imidazolinen-(2) und deren Säureadditionssalzen
DE855852C (de)	1952-11-17	Verfahren zur Herstellung eines neuen Imidazolins
DE1941761C3 (de)	1976-08-19	2-(Thienyl-3 '-amino) -1.3-diazacyclopentene und Verfahren zu ihrer Herstellung
AT228199B (de)	1963-07-10	Verfahren zur Herstellung eines neuen Imidazolinderivates und seiner Salze
AT258950B (de)	1967-12-27	Verfahren zur Herstellung von neuen substituierten Guanidinverbindungen
AT293423B (de)	1971-10-11	Verfahren zur Herstellung von substituierten Acetylguanidinen und ihren Säureadditionssalzen
DE1595875C (de)	1972-08-31	Phenothiazine und Verfahren zu deren Herstellung