IL27999A - Naphthyl-and tetrahydronaphthyl-formamidines - Google Patents

Naphthyl-and tetrahydronaphthyl-formamidines

Info

Publication number: IL27999A
Authority: IL; Israel
Prior art keywords: general formula; reaction; derivatives; naphthyl; quaternary ammonium
Prior art date: 1966-05-25

Application number

IL27999A

Other languages

English (en)

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1966-05-25

Filing date

1967-05-17

Publication date

1971-08-25

1967-05-17 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1971-08-25 Publication of IL27999A publication Critical patent/IL27999A/en

Links

YLUBXIQMMDJLLC-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carboximidamide Chemical class C1=CC=C2C(C(=N)N)CCCC2=C1 YLUBXIQMMDJLLC-UHFFFAOYSA-N 0.000 title claims 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
238000000034 method Methods 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
150000001875 compounds Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 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
239000000126 substance Substances 0.000 claims description 2
239000000654 additive Substances 0.000 claims 1
150000003863 ammonium salts Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000004970 halomethyl group Chemical group 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000155 melt Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
-1 naphthyl formamidine derivatives Chemical class 0.000 description 3
239000000047 product Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
230000000507 anthelmentic effect Effects 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000002474 Tinea Diseases 0.000 description 1
241000893966 Trichophyton verrucosum Species 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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)
Hydrogenated Pyridines (AREA)

IL27999A 1966-05-25 1967-05-17 Naphthyl-and tetrahydronaphthyl-formamidines IL27999A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUEE001250		1966-05-25

Publications (1)

Publication Number	Publication Date
IL27999A true IL27999A (en)	1971-08-25

Family

ID=10995194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL27999A IL27999A (en)	1966-05-25	1967-05-17	Naphthyl-and tetrahydronaphthyl-formamidines

Country Status (12)

Country	Link
US (1)	US3539631A (de)
AT (1)	AT274784B (de)
BE (1)	BE699038A (de)
CH (1)	CH484878A (de)
CS (1)	CS157021B2 (de)
DE (1)	DE1618317B2 (de)
DK (1)	DK126109B (de)
FR (1)	FR6329M (de)
GB (1)	GB1144039A (de)
IL (1)	IL27999A (de)
NL (1)	NL148045B (de)
SE (1)	SE354063B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4644065A (en) *	1984-05-15	1987-02-17	Merrell Dow Pharmaceuticals Inc.	Process for the preparation of 4(3H)-quinazolinones
DK0874625T3 (da)	1996-01-22	2005-06-20	Lilly Co Eli	Indanderivater til antipsykotiske præparater
WO1998031660A1 (en) *	1997-01-22	1998-07-23	Eli Lilly And Company	Process for preparing indane-like compounds
JP2001510797A (ja)	1997-07-22	2001-08-07	イーライ・リリー・アンド・カンパニー	医薬化合物
WO2004087124A1 (en) *	2003-03-29	2004-10-14	Mitsubishi Pharma Corporation	Compounds having serotonin 5-ht17 receptor antagonist activity and muscarinic m4 receptor agonist activity and their use in the treatment of psychotic disorders
WO2017067839A1 (en) *	2015-10-23	2017-04-27	Syngenta Participations Ag	Microbiocidal phenylamidine derivatives

1967
- 1967-05-17 IL IL27999A patent/IL27999A/en unknown
- 1967-05-18 DE DE1967E0034005 patent/DE1618317B2/de active Granted
- 1967-05-18 GB GB23067/67A patent/GB1144039A/en not_active Expired
- 1967-05-18 AT AT465067A patent/AT274784B/de active
- 1967-05-24 FR FR107547A patent/FR6329M/fr not_active Expired
- 1967-05-24 CS CS377067A patent/CS157021B2/cs unknown
- 1967-05-24 DK DK271367AA patent/DK126109B/da unknown
- 1967-05-24 US US640806A patent/US3539631A/en not_active Expired - Lifetime
- 1967-05-24 SE SE07285/67A patent/SE354063B/xx unknown
- 1967-05-25 NL NL676707275A patent/NL148045B/xx not_active IP Right Cessation
- 1967-05-25 CH CH735167A patent/CH484878A/de not_active IP Right Cessation
- 1967-05-25 BE BE699038D patent/BE699038A/xx unknown

Also Published As

Publication number	Publication date
DE1618317A1 (de)	1970-12-23
CH484878A (de)	1970-01-31
CS157021B2 (de)	1974-08-23
FR6329M (de)	1968-09-23
SE354063B (de)	1973-02-26
DE1618317B2 (de)	1977-06-16
BE699038A (de)	1967-11-03
NL148045B (nl)	1975-12-15
DK126109B (da)	1973-06-12
NL6707275A (de)	1967-11-27
AT274784B (de)	1969-09-25
GB1144039A (en)	1969-03-05
US3539631A (en)	1970-11-10

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US3539631A (en)	1970-11-10	New naphthyl- and tetrahydronaphthyl formamdines
IL103229A (en)	1996-09-12	Imidazolylmethyl-pyridine derivatives their preparation and pharmaceutical compositions containing them
Beyerman et al.	1955	Synthetic neuromuscular‐and ganglion‐blocking agents. N‐Alkylated bipyridyls, bipiperidyls, and their methylene and ethylene “homologues”
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US3056784A (en)	1962-10-02	Substituted 5, 6-dihydro-2(1h)-pyrazinones
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US3328406A (en)	1967-06-27	Amide and piperazides of carbazole-9-glyoxylic acid
US3991066A (en)	1976-11-09	1,3,4,9B-Tetrahydro-5-methyl-2H-indeno[1,2-c]pyridines
US3244725A (en)	1966-04-05	4, 5-diacyl-3-hydroxy-3-pyrrolin-2-ones
US3433802A (en)	1969-03-18	3-(n-lower-alkylanilino)pyrrolidines
SU523641A3 (ru)	1976-07-30	Способ получени имидазогетероциклических соединений или их солей
US3193579A (en)	1965-07-06	Terephthalamides and intermediates useful in preparing same
US2802826A (en)	1957-08-13	Octahydro-pyrido [4, 3-d] pyrimidine compounds
Dillard et al.	1968	Acetylenic carbamates. III. The N-cycloaliphatic derivatives