GB1044304A - Pregneno- and pregnadieno-[3,2-c]pyrazoles - Google Patents
Pregneno- and pregnadieno-[3,2-c]pyrazolesInfo
- Publication number
- GB1044304A GB1044304A GB22828/63A GB2282863A GB1044304A GB 1044304 A GB1044304 A GB 1044304A GB 22828/63 A GB22828/63 A GB 22828/63A GB 2282863 A GB2282863 A GB 2282863A GB 1044304 A GB1044304 A GB 1044304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoro
- pregnadien
- hydroxy
- prepared
- compounds
- 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
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- -1 alkali metal salts Chemical group 0.000 abstract 4
- 150000003431 steroids Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 3
- 239000011737 fluorine Chemical group 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000012445 acidic reagent Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 2
- AVKZYESHFHYAMY-SBNILOIZSA-N (8R,9S,10R,13S,14S)-10,13-dimethyl-17-(oxiran-2-yl)-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound O1CC1C1=CC[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O AVKZYESHFHYAMY-SBNILOIZSA-N 0.000 abstract 1
- AGDIEJFBSYNAFO-KGWSWXIGSA-N (8S,9S,10R,13S,14S)-10,13-dimethyl-17-propylidene-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound CCC=C1CC[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O AGDIEJFBSYNAFO-KGWSWXIGSA-N 0.000 abstract 1
- LGTNVTBMTQCJMS-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 LGTNVTBMTQCJMS-BYZMTCBYSA-N 0.000 abstract 1
- UOQFZGVGGMHGEE-UHFFFAOYSA-N 1,1-dihydroxypropan-2-one Chemical group CC(=O)C(O)O UOQFZGVGGMHGEE-UHFFFAOYSA-N 0.000 abstract 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- UOCHRIGXPHALME-YHHUUVGUSA-N 2-[(8R,9S,10R,13S,14S,16R)-16-fluoro-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate Chemical compound C(C)(=O)OCC=C1[C@@H](C[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)F UOCHRIGXPHALME-YHHUUVGUSA-N 0.000 abstract 1
- CTTGNKOOSCSKJB-YHHUUVGUSA-N 2-[(8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate Chemical compound C(C)(=O)OCC=C1[C@@H](C[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)O CTTGNKOOSCSKJB-YHHUUVGUSA-N 0.000 abstract 1
- KYLJINXWEPMQAV-FADBTOOJSA-N 2-[(8S,9S,10R,13S,14S)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate Chemical compound C(C)(=O)OCC=C1CC[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O KYLJINXWEPMQAV-FADBTOOJSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- 241000790917 Dioxys <bee> Species 0.000 abstract 1
- SCOFRDCTIQDONL-ROSOUBNMSA-N F[C@H]1C[C@H]2[C@@H]3CCC(=CCOC(C)=O)[C@]3(CC[C@@H]2[C@]2(CCC(C=C12)=O)C)C Chemical compound F[C@H]1C[C@H]2[C@@H]3CCC(=CCOC(C)=O)[C@]3(CC[C@@H]2[C@]2(CCC(C=C12)=O)C)C SCOFRDCTIQDONL-ROSOUBNMSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- SGETXHDECYGJPQ-BIPPRZMMSA-N [2-chloro-2-[(8R,9S,10R,13S,14S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] acetate Chemical compound ClC(COC(C)=O)C1=CC[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O SGETXHDECYGJPQ-BIPPRZMMSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical group OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 abstract 1
- 229940019931 silver phosphate Drugs 0.000 abstract 1
- 229910000161 silver phosphate Inorganic materials 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/008—Ketals at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16
- C07J7/0055—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
- C07J7/0075—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified substituted in position 17 alfa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0047—Nitrogen only at position 2(3)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US203748A US3148183A (en) | 1962-06-20 | 1962-06-20 | Delta4 and delta4, 6-17alpha-acyloxy-20-oxo-steroid-[3, 2-c] pyrazoles of the pregnane series |
| US26230463A | 1963-03-04 | 1963-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1044304A true GB1044304A (en) | 1966-09-28 |
Family
ID=26898869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22828/63A Expired GB1044304A (en) | 1962-06-20 | 1963-06-07 | Pregneno- and pregnadieno-[3,2-c]pyrazoles |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3148183A (en, 2012) |
| BE (1) | BE633906A (en, 2012) |
| BR (1) | BR6349964D0 (en, 2012) |
| CH (1) | CH462178A (en, 2012) |
| DE (1) | DE1468265A1 (en, 2012) |
| FR (2) | FR1552757A (en, 2012) |
| GB (1) | GB1044304A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010147947A2 (en) | 2009-06-16 | 2010-12-23 | Schering Corporation | NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS, COMPOSITIONS AND USES THEREOF |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325480A (en) * | 1964-02-01 | 1967-06-13 | Ormonoterapia Richter Spa | 5'-substituted steroidal pyrazoles of the pregnane series |
| US3530117A (en) * | 1969-01-09 | 1970-09-22 | Merck & Co Inc | Delta**4 and delta**4,6 - 17 - hydroxy - steroidal pyrazoles of the pregnane series |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945852A (en) * | 1959-05-20 | 1960-07-19 | Searle & Co | 17-oxygenated 9alpha-substituted androstano [3, 2-c] pyrazoles and derivatives |
-
0
- BE BE633906D patent/BE633906A/xx unknown
-
1962
- 1962-06-20 US US203748A patent/US3148183A/en not_active Expired - Lifetime
-
1963
- 1963-06-07 GB GB22828/63A patent/GB1044304A/en not_active Expired
- 1963-06-14 DE DE19631468265 patent/DE1468265A1/de active Pending
- 1963-06-18 BR BR149964/63A patent/BR6349964D0/pt unknown
- 1963-06-19 FR FR938682A patent/FR1552757A/fr not_active Expired
- 1963-06-20 CH CH773463A patent/CH462178A/de unknown
- 1963-09-18 FR FR947928A patent/FR4030M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010147947A2 (en) | 2009-06-16 | 2010-12-23 | Schering Corporation | NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS, COMPOSITIONS AND USES THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| US3148183A (en) | 1964-09-08 |
| FR4030M (en, 2012) | 1966-03-28 |
| DE1468265A1 (de) | 1969-11-20 |
| FR1552757A (en, 2012) | 1969-01-10 |
| BR6349964D0 (pt) | 1973-07-03 |
| CH462178A (de) | 1968-09-15 |
| BE633906A (en, 2012) |
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