CH433247A - Verfahren zur Herstellung von in 1-Stellung substituierten 3-Cyanguanidinen - Google Patents

Verfahren zur Herstellung von in 1-Stellung substituierten 3-Cyanguanidinen

Info

Publication number: CH433247A
Authority: CH; Switzerland
Prior art keywords: substituted; cyanguanidines; tert; acid; blood pressure
Prior art date: 1962-11-07

Application number

CH1359663A

Other languages

German (de)

English (en)

Inventor

Rhodes Cummings John

Cohen Elliott

Original Assignee

American Cyanamid Co

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.)

1962-11-07

Filing date

1963-11-06

Publication date

1967-04-15

1963-11-06 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1967-04-15 Publication of CH433247A publication Critical patent/CH433247A/de

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 3
230000036772 blood pressure Effects 0.000 claims description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
239000011707 mineral Substances 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
QWJNFFYFEKXZBF-UHFFFAOYSA-N cyanocyanamide Chemical compound N#CNC#N QWJNFFYFEKXZBF-UHFFFAOYSA-N 0.000 claims description 3
230000010412 perfusion Effects 0.000 claims description 3
BFUITLGNKICXGA-UHFFFAOYSA-N 2,4-dimethylpentan-2-amine Chemical compound CC(C)CC(C)(C)N BFUITLGNKICXGA-UHFFFAOYSA-N 0.000 claims description 2
GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical group CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 1
230000000694 effects Effects 0.000 description 11
206010020772 Hypertension Diseases 0.000 description 9
-1 1-substituted 3-cyanguanidine Chemical class 0.000 description 8
241000282472 Canis lupus familiaris Species 0.000 description 7
241000700159 Rattus Species 0.000 description 6
230000004872 arterial blood pressure Effects 0.000 description 5
102000015427 Angiotensins Human genes 0.000 description 4
108010064733 Angiotensins Proteins 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
230000037213 diet Effects 0.000 description 4
235000005911 diet Nutrition 0.000 description 4
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
229930182837 (R)-adrenaline Natural products 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000003276 anti-hypertensive effect Effects 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
229960005139 epinephrine Drugs 0.000 description 3
230000001631 hypertensive effect Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000005555 hypertensive agent Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
230000036513 peripheral conductance Effects 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
210000002254 renal artery Anatomy 0.000 description 2
230000004044 response Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000002792 vascular Effects 0.000 description 2
239000005526 vasoconstrictor agent Substances 0.000 description 2
KPNJYXKRHWAPHP-UHFFFAOYSA-N 2-methylpentan-2-amine Chemical compound CCCC(C)(C)N KPNJYXKRHWAPHP-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
238000012935 Averaging Methods 0.000 description 1
239000005711 Benzoic acid Substances 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
208000001953 Hypotension Diseases 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
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002472 Starch Polymers 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
235000011054 acetic acid Nutrition 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940124572 antihypotensive agent Drugs 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
210000000702 aorta abdominal Anatomy 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000008321 arterial blood flow Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
238000009530 blood pressure measurement Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000011161 development Methods 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000003414 extremity Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000000574 ganglionic effect Effects 0.000 description 1
238000003304 gavage Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
VZVGEDRCVUKSEL-UHFFFAOYSA-N guancidine Chemical compound CCC(C)(C)N=C(N)NC#N VZVGEDRCVUKSEL-UHFFFAOYSA-N 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
210000003090 iliac artery Anatomy 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
238000010837 poor prognosis Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1359663A 1962-11-07 1963-11-06 Verfahren zur Herstellung von in 1-Stellung substituierten 3-Cyanguanidinen CH433247A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US23613362A	1962-11-07	1962-11-07

Publications (1)

Publication Number	Publication Date
CH433247A true CH433247A (de)	1967-04-15

Family

ID=22888258

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1359663A CH433247A (de)	1962-11-07	1963-11-06	Verfahren zur Herstellung von in 1-Stellung substituierten 3-Cyanguanidinen

Country Status (7)

Country	Link
BR (1)	BR6354400D0 (fr)
CH (1)	CH433247A (fr)
DE (1)	DE1443386C3 (fr)
ES (1)	ES293287A1 (fr)
FR (1)	FR2977M (fr)
GB (1)	GB995398A (fr)
MY (1)	MY6900093A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3729530A1 (de) *	1987-09-04	1989-03-16	Degussa	Verfahren zur herstellung von 1,6-di(n(pfeil hoch)3(pfeil hoch)-cyano-n(pfeil hoch)1(pfeil hoch)-guanidino)hexan

1963
- 1963-10-15 GB GB40698/63A patent/GB995398A/en not_active Expired
- 1963-10-17 FR FR950857A patent/FR2977M/fr active Active
- 1963-11-06 BR BR154400/63A patent/BR6354400D0/pt unknown
- 1963-11-06 CH CH1359663A patent/CH433247A/de unknown
- 1963-11-07 DE DE1443386A patent/DE1443386C3/de not_active Expired
- 1963-11-07 ES ES293287A patent/ES293287A1/es not_active Expired
1969
- 1969-12-31 MY MY196993A patent/MY6900093A/xx unknown

Also Published As

Publication number	Publication date
ES293287A1 (es)	1964-04-01
BR6354400D0 (pt)	1973-07-19
MY6900093A (en)	1969-12-31
DE1443386B2 (de)	1973-06-20
DE1443386C3 (de)	1974-01-24
FR2977M (fr)	1964-11-30
GB995398A (en)	1965-06-16
DE1443386A1 (de)	1969-01-30

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DE2120495C2 (de)	1982-06-03	2-Methyl-2-hydroxypropyl-4-(4-amino-6,7,8-trimethoxychinazolin-2-yl)-1-piperazincarboxylat
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