GB915454A - Nitrogen mustards - Google Patents
Nitrogen mustardsInfo
- Publication number
- GB915454A GB915454A GB2267260A GB2267260A GB915454A GB 915454 A GB915454 A GB 915454A GB 2267260 A GB2267260 A GB 2267260A GB 2267260 A GB2267260 A GB 2267260A GB 915454 A GB915454 A GB 915454A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- group
- atom
- halogen
- salt
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title 2
- 229910052757 nitrogen Inorganic materials 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 239000000460 chlorine Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- LIEXBIUWTRUWKB-UHFFFAOYSA-N N,N-diethyl-4-isocyanatoaniline hydrochloride Chemical compound Cl.C(C)N(CC)C1=CC=C(C=C1)N=C=O LIEXBIUWTRUWKB-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- ZNZNXSDPNKCWNO-UHFFFAOYSA-N S.CO Chemical compound S.CO ZNZNXSDPNKCWNO-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- GTRLQRHWPXEBLF-UHFFFAOYSA-N benzyl carbamimidothioate Chemical compound NC(=N)SCC1=CC=CC=C1 GTRLQRHWPXEBLF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 238000007918 intramuscular administration Methods 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of formula R1.Q.CO.Q1.R in which R1 represents a group (X.CH2CH2)2N-Ar-, X representing a chlorine or bromine atom and Ar representing a p-phenylene group, Q and Q1 each represent an oxygen atom, a sulphur atom or an -NH- group and may be the same or different, and R represents a sugar residue, an aryl group different from R1 or a lower (i.e. 1-4 carbon atom) alkyl group, said aryl or lower alkyl group being substituted by a saltforming group; and their derivatives in which the salt-forming group is converted into a salt or ester. In examples, the sugar residue is D-galactose and 1,2:3,4-di-O-isopropylidene-D-galactose, and the salt forming group carboxyl, phenolic hydroxy, amino and dialkylamino; derivatives obtained are alkyl esters, and salts, for example methiodide, S-benzylthiouronium and picrate salts. Methods of preparation referred to are the reaction of compounds R1.QH and OCN.R (Q1=NH); of compounds R1.Q.CO.halogen and H2N.R (Q1=NH); of compounds R1.QH and halogen.COOR (Q1=O); of compounds R1.QH and Cl.CO.S.R (Q1=S); and of compounds R.SH and R1.NCO, R1.O.CO.Cl or R1.S.CO.Cl (Q1=S). p - N,N - Diethylaminophenyl isocyanate hydrochloride is prepared by the action of phosgene on the corresponding aniline. In the Provisional Specification X represents any halogen atom. Pharmaceutical compositions comprise one or more of the compounds of the invention dissolved in a compatible fluid carrier, for injection. Intramuscular and interperitoneal administration are mentioned. The compounds have anti-tumour activity.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2267260A GB915454A (en) | 1960-06-28 | 1960-06-28 | Nitrogen mustards |
| FR866190A FR1463764A (en) | 1960-06-28 | 1961-06-27 | Process for the preparation of nitrogen mustard-type compounds |
| CH756161A CH407147A (en) | 1960-06-28 | 1961-06-28 | Process for the preparation of anti-tumor compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2267260A GB915454A (en) | 1960-06-28 | 1960-06-28 | Nitrogen mustards |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB915454A true GB915454A (en) | 1963-01-16 |
Family
ID=10183233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2267260A Expired GB915454A (en) | 1960-06-28 | 1960-06-28 | Nitrogen mustards |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH407147A (en) |
| FR (1) | FR1463764A (en) |
| GB (1) | GB915454A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118290306A (en) * | 2024-04-02 | 2024-07-05 | 西南科技大学 | A novel nitrogen mustard derivative and its preparation method |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ268629A (en) * | 1993-07-15 | 1997-10-24 | Cancer Res Campaign Tech | Prodrugs of protein tyrosine kinase inhibitors; such compounds linked to a protecting group capable of being cleaved to release the inhibitor |
| GB9315494D0 (en) * | 1993-07-27 | 1993-09-08 | Springer Caroline | Improvements relating to prodrugs |
| GB9501052D0 (en) * | 1995-01-19 | 1995-03-08 | Cancer Res Campaign Tech | Improvements relating to prodrugs |
-
1960
- 1960-06-28 GB GB2267260A patent/GB915454A/en not_active Expired
-
1961
- 1961-06-27 FR FR866190A patent/FR1463764A/en not_active Expired
- 1961-06-28 CH CH756161A patent/CH407147A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118290306A (en) * | 2024-04-02 | 2024-07-05 | 西南科技大学 | A novel nitrogen mustard derivative and its preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| CH407147A (en) | 1966-02-15 |
| FR1463764A (en) | 1966-07-22 |
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