CA1117015A - Procede de production d'un produit pharmaceutique detoxifie contenant un agent alkylant a action cytostatique - Google Patents
Procede de production d'un produit pharmaceutique detoxifie contenant un agent alkylant a action cytostatiqueInfo
- Publication number
- CA1117015A CA1117015A CA000317744A CA317744A CA1117015A CA 1117015 A CA1117015 A CA 1117015A CA 000317744 A CA000317744 A CA 000317744A CA 317744 A CA317744 A CA 317744A CA 1117015 A CA1117015 A CA 1117015A
- Authority
- CA
- Canada
- Prior art keywords
- mercapto
- sulfonic acid
- chloroethyl
- alkylating agent
- 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
- 229940100198 alkylating agent Drugs 0.000 title claims abstract description 30
- 239000002168 alkylating agent Substances 0.000 title claims abstract description 30
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 11
- 229940127557 pharmaceutical product Drugs 0.000 title claims description 9
- 238000000034 method Methods 0.000 title abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 229910006069 SO3H Inorganic materials 0.000 claims abstract 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkali metal salt Chemical class 0.000 claims description 10
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims description 10
- 229960001101 ifosfamide Drugs 0.000 claims description 10
- 229940006193 2-mercaptoethanesulfonic acid Drugs 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 claims description 7
- 229960000875 trofosfamide Drugs 0.000 claims description 6
- ZSZKJARKHWCBJK-UHFFFAOYSA-N 2-[[3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl]amino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNP1(=O)OCCCN1CCCl ZSZKJARKHWCBJK-UHFFFAOYSA-N 0.000 claims description 4
- 229950008275 sufosfamide Drugs 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 1
- 230000001085 cytostatic effect Effects 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
- 239000000824 cytostatic agent Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 14
- 210000003932 urinary bladder Anatomy 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 10
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 6
- 229960004397 cyclophosphamide Drugs 0.000 description 6
- 239000002207 metabolite Substances 0.000 description 6
- 210000001635 urinary tract Anatomy 0.000 description 6
- 238000001784 detoxification Methods 0.000 description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 4
- 229940090044 injection Drugs 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- 229960004308 acetylcysteine Drugs 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- OKVLRTXOHOBONS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropane-1-sulfonic acid Chemical compound SCC(C)CS(O)(=O)=O OKVLRTXOHOBONS-UHFFFAOYSA-N 0.000 description 1
- OBDVFOBWBHMJDG-UHFFFAOYSA-N 3-mercapto-1-propanesulfonic acid Chemical compound OS(=O)(=O)CCCS OBDVFOBWBHMJDG-UHFFFAOYSA-N 0.000 description 1
- HMEJBVOVTCTWRG-UHFFFAOYSA-N 6-sulfanylhexane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCCCS HMEJBVOVTCTWRG-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MRIMWDXKBILRPB-UHFFFAOYSA-N O=P1NCCCO1 Chemical class O=P1NCCCO1 MRIMWDXKBILRPB-UHFFFAOYSA-N 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- COSZWAUYIUYQBS-UHFFFAOYSA-B hexapotassium hexasodium 3-carboxy-3-hydroxypentanedioate 2-hydroxypropane-1,2,3-tricarboxylate hydrate Chemical compound O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[K+].[K+].[K+].[K+].[K+].[K+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O COSZWAUYIUYQBS-UHFFFAOYSA-B 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229960004560 triaziquone Drugs 0.000 description 1
- PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2756018.5 | 1977-12-14 | ||
| DE2756018A DE2756018C2 (de) | 1977-12-14 | 1977-12-14 | Verwendung von Salzen von Mercaptoalkansulfonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1117015A true CA1117015A (fr) | 1982-01-26 |
Family
ID=6026256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000317744A Expired CA1117015A (fr) | 1977-12-14 | 1978-12-12 | Procede de production d'un produit pharmaceutique detoxifie contenant un agent alkylant a action cytostatique |
Country Status (15)
| Country | Link |
|---|---|
| AR (1) | AR216563A1 (fr) |
| AT (1) | AT358162B (fr) |
| CA (1) | CA1117015A (fr) |
| DD (1) | DD140420B5 (fr) |
| DE (1) | DE2756018C2 (fr) |
| EG (1) | EG14057A (fr) |
| GR (1) | GR68356B (fr) |
| HU (1) | HU179915B (fr) |
| IE (1) | IE47609B1 (fr) |
| IL (1) | IL56097A (fr) |
| MC (1) | MC1229A1 (fr) |
| PL (1) | PL211758A1 (fr) |
| PT (1) | PT68904A (fr) |
| YU (1) | YU291978A (fr) |
| ZA (1) | ZA786662B (fr) |
-
1977
- 1977-12-14 DE DE2756018A patent/DE2756018C2/de not_active Expired
-
1978
- 1978-11-27 ZA ZA00786662A patent/ZA786662B/xx unknown
- 1978-11-29 GR GR57769A patent/GR68356B/el unknown
- 1978-11-30 IL IL56097A patent/IL56097A/xx unknown
- 1978-12-05 IE IE2404/78A patent/IE47609B1/en unknown
- 1978-12-06 AT AT871078A patent/AT358162B/de not_active IP Right Cessation
- 1978-12-06 AR AR274705A patent/AR216563A1/es active
- 1978-12-12 DD DD20969178A patent/DD140420B5/de active IP Right Maintenance
- 1978-12-12 CA CA000317744A patent/CA1117015A/fr not_active Expired
- 1978-12-12 MC MC781346A patent/MC1229A1/fr unknown
- 1978-12-12 PT PT68904A patent/PT68904A/pt unknown
- 1978-12-13 HU HU78AA913A patent/HU179915B/hu unknown
- 1978-12-13 EG EG702/78A patent/EG14057A/xx active
- 1978-12-14 PL PL21175878A patent/PL211758A1/xx unknown
- 1978-12-16 YU YU02919/78A patent/YU291978A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA871078A (de) | 1980-01-15 |
| GR68356B (fr) | 1981-12-23 |
| IL56097A (en) | 1981-09-13 |
| MC1229A1 (fr) | 1979-10-26 |
| DE2756018B1 (de) | 1979-03-29 |
| AT358162B (de) | 1980-08-25 |
| YU291978A (en) | 1984-02-29 |
| IL56097A0 (en) | 1979-01-31 |
| IE47609B1 (en) | 1984-05-02 |
| DD140420B5 (de) | 1995-06-14 |
| ZA786662B (en) | 1979-10-31 |
| EG14057A (en) | 1982-09-30 |
| PT68904A (en) | 1979-01-01 |
| DD140420A5 (de) | 1980-03-05 |
| PL211758A1 (fr) | 1980-02-11 |
| AR216563A1 (es) | 1979-12-28 |
| DE2756018C2 (de) | 1979-11-22 |
| IE782404L (en) | 1979-06-14 |
| HU179915B (en) | 1983-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |