ATE131812T1 - Verfahren zur totalen synthese von einer indol- struktur-verbindungsklasse des tryptamin-typs, insbesondere melatonin- oder n-acetyl-5- methoxytryptamin mit hoher reinheit und löslichkeit, verwendbar in der aids-therapie - Google Patents

Verfahren zur totalen synthese von einer indol- struktur-verbindungsklasse des tryptamin-typs, insbesondere melatonin- oder n-acetyl-5- methoxytryptamin mit hoher reinheit und löslichkeit, verwendbar in der aids-therapie

Info

Publication number: ATE131812T1
Authority: AT; Austria
Prior art keywords: acetyl; melatonine; methoxytriptamine; order; total synthesis
Prior art date: 1988-02-25

Application number

AT89830055T

Other languages

English (en)

Inventor

Franco Fraschini

Bella Luigi Di

Ermanno Duranti

Original Assignee

I F L O S A S Di Giorgio E Ald

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.)

1988-02-25

Filing date

1989-02-16

Publication date

1996-01-15

1988-02-25 Priority claimed from IT19549/88A external-priority patent/IT1217344B/it

1988-09-08 Priority claimed from IT8821872A external-priority patent/IT1230493B/it

1989-02-16 Application filed by I F L O S A S Di Giorgio E Ald filed Critical I F L O S A S Di Giorgio E Ald

1996-01-15 Application granted granted Critical

1996-01-15 Publication of ATE131812T1 publication Critical patent/ATE131812T1/de

Links

YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 title abstract 7
DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 title abstract 7
229960003987 melatonin Drugs 0.000 title abstract 6
238000000034 method Methods 0.000 title abstract 5
208000030507 AIDS Diseases 0.000 title abstract 3
238000006257 total synthesis reaction Methods 0.000 title abstract 3
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 title abstract 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
238000002560 therapeutic procedure Methods 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
VJYUMIOXHJSLEZ-UHFFFAOYSA-N 3-[3-[2-(1,3-dioxoisoindol-2-yl)ethyl]-5-methoxy-1h-indol-2-yl]propanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1=C(CCC(O)=O)NC2=CC=C(OC)C=C21 VJYUMIOXHJSLEZ-UHFFFAOYSA-N 0.000 abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 abstract 2
230000001173 tumoral effect Effects 0.000 abstract 2
ARITXYXYCOZKMU-UHFFFAOYSA-N 2,2-dibromopropane Chemical compound CC(C)(Br)Br ARITXYXYCOZKMU-UHFFFAOYSA-N 0.000 abstract 1
RGDXUHMBHOZVCX-UHFFFAOYSA-N 3-(3-bromopropyl)benzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=CC(CCCBr)=C1C(N)=O RGDXUHMBHOZVCX-UHFFFAOYSA-N 0.000 abstract 1
LOFQVCFHMGJYIS-UHFFFAOYSA-N 4-(diazomethoxy)aniline Chemical compound NC1=CC=C(OC=[N+]=[N-])C=C1 LOFQVCFHMGJYIS-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
NXSHODVXBOPCHO-UHFFFAOYSA-N benzene-1,2-dicarboxamide;potassium Chemical compound [K].NC(=O)C1=CC=CC=C1C(N)=O NXSHODVXBOPCHO-UHFFFAOYSA-N 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
125000001041 indolyl group Chemical group 0.000 abstract 1
229910052708 sodium Inorganic materials 0.000 abstract 1
239000011734 sodium Substances 0.000 abstract 1
235000011149 sulphuric acid Nutrition 0.000 abstract 1
230000001225 therapeutic effect Effects 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 abstract 1
229960002555 zidovudine Drugs 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

AT89830055T 1988-02-25 1989-02-16 Verfahren zur totalen synthese von einer indol- struktur-verbindungsklasse des tryptamin-typs, insbesondere melatonin- oder n-acetyl-5- methoxytryptamin mit hoher reinheit und löslichkeit, verwendbar in der aids-therapie ATE131812T1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT19549/88A IT1217344B (it)	1988-02-25	1988-02-25	Farmaco per la cura delle sindrome di immunodeficienza acquisita
IT8821872A IT1230493B (it)	1988-09-08	1988-09-08	Procedimento di sintesi totale, per l'ottenimento di una categoria di prodotti derivati a struttura indolica del tipo della triptamina in particolare di melatonina o n-aceti 5-metossitriptamina ad elevato grado di purezza e facilmente solubile utilizzabile in specie per impieghi terapeutici e quale farmaco per la cura delle sindromi da

Publications (1)

Publication Number	Publication Date
ATE131812T1 true ATE131812T1 (de)	1996-01-15

Family

ID=26327207

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT89830055T ATE131812T1 (de)	1988-02-25	1989-02-16	Verfahren zur totalen synthese von einer indol- struktur-verbindungsklasse des tryptamin-typs, insbesondere melatonin- oder n-acetyl-5- methoxytryptamin mit hoher reinheit und löslichkeit, verwendbar in der aids-therapie

Country Status (7)

Country	Link
US (2)	US5122535A (de)
EP (1)	EP0330625B1 (de)
JP (1)	JP2724493B2 (de)
AT (1)	ATE131812T1 (de)
DE (1)	DE68925135T2 (de)
ES (1)	ES2083390T3 (de)
GR (1)	GR3019365T3 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2830010A1 (fr) *	2001-09-27	2003-03-28	Atofina	Procede de preparation de n-(omega-bromoalkyl)phtalimides
FR2830011A1 (fr) *	2001-09-27	2003-03-28	Atofina	Procede de preparation de n-(omega-bromoalkyl)phtalimides
KR100411599B1 (ko) *	2001-10-23	2003-12-18	동방에프티엘 주식회사	5-치환된 인돌 유도체의 제조방법
US20050020666A1 (en) *	2003-07-25	2005-01-27	Dabur Research Foundation	Cardioprotective agents
EP2616439B1 (de) *	2010-09-14	2015-12-16	Council of Scientific & Industrial Research	Tryptaminderivate, ihre zubereitung und ihre verwendung in der gastropathie
CN110818610B (zh) *	2019-12-06	2021-03-23	杭州志源生物科技有限公司	褪黑素的制备方法
CN115010645B (zh) *	2022-06-21	2023-08-29	广西师范大学	一种褪黑素的制备方法
WO2024138007A2 (en) *	2022-12-21	2024-06-27	Caamtech, Inc.	Tryptamine derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2248155A (en) *	1938-06-28	1941-07-08	Merck & Co Inc	Process for the production of indole acids
US2416258A (en) *	1944-03-17	1947-02-18	Purdue Research Foundation	3-(5-ethoxy-3-indolyl)-propyl compounds
CH585199A5 (de) *	1972-09-15	1977-02-28	Siegfried Ag
DE3105850A1 (de) *	1981-02-18	1982-08-19	Horst, Hans Jörg, Priv.Doz.Dr., 2057 Reinbek	Mittel zum behandeln von tumoren

1989
- 1989-02-16 DE DE68925135T patent/DE68925135T2/de not_active Expired - Fee Related
- 1989-02-16 ES ES89830055T patent/ES2083390T3/es not_active Expired - Lifetime
- 1989-02-16 EP EP89830055A patent/EP0330625B1/de not_active Expired - Lifetime
- 1989-02-16 AT AT89830055T patent/ATE131812T1/de not_active IP Right Cessation
- 1989-02-17 US US07/312,627 patent/US5122535A/en not_active Ceased
- 1989-02-23 JP JP1045068A patent/JP2724493B2/ja not_active Expired - Lifetime
1994
- 1994-06-02 US US08/252,905 patent/USRE35631E/en not_active Expired - Lifetime
1996
- 1996-03-19 GR GR960400765T patent/GR3019365T3/el unknown

Also Published As

Publication number	Publication date
GR3019365T3 (en)	1996-06-30
US5122535A (en)	1992-06-16
EP0330625A2 (de)	1989-08-30
EP0330625A3 (de)	1991-09-18
DE68925135T2 (de)	1996-08-01
EP0330625B1 (de)	1995-12-20
JPH023680A (ja)	1990-01-09
DE68925135D1 (de)	1996-02-01
JP2724493B2 (ja)	1998-03-09
USRE35631E (en)	1997-10-14
ES2083390T3 (es)	1996-04-16

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Legal Events

Date	Code	Title	Description
1996-07-15	UEP	Publication of translation of european patent specification
2000-11-15	REN	Ceased due to non-payment of the annual fee